


Changes (Turn and Face the Strange)

by Navajo_Woman (NavajoLovesDestiel)



Category: Supernatural
Genre: AU, Anal Fingering, Anal Sex, Angst, F/M, Fluff, MTF Castiel, Mention of Past Violence, Other, Smut, Transgender, mention of past rape
Language: English
Status: Completed
Published: 2016-08-17
Updated: 2016-09-28
Packaged: 2018-08-09 09:35:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 20
Words: 27,952
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7796731
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/Navajo_Woman
Summary: <blockquote class="userstuff">
              <p>Cassie Novak is a male to female transgender who very tentatively agrees to go on one date with Dean Winchester. She has every intention of never going on a second date. But things have a way of not working out the way she planned.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> If you are bothered in any way with the idea of Castiel being transgender, please don't read this. 
> 
> There is a brief mention of a past rape and past violence. There will be a mention of this before the chapter if you want to skip it.
> 
> We will update regularly and there will be a happy ending.

Dean saw her the moment she walked into the bar.  She was tall, at least five eleven in flats.  She dressed in black hose, a short black leather skirt and a blood red silk blouse which was open just enough to show off her gorgeous tits.  Her hair was fairly short, dark and messy.  She looked like she had just gotten out of bed, actually.

She walked to the bar and took a seat, crossing her beautiful legs.  Dean almost had to check for drool as he realized he was staring.  She glanced around and when their eyes met albeit only briefly, he noted the most beautiful blue hue he had ever seen. He didn’t even have a name for the color they were. 

She ordered a glass of white wine and sipped it, keeping her eyes down.  It didn’t look to Dean like she was waiting for or looking for anyone in particular, and the more he stared at her body, her beautiful face, and that amazing messy hair, the more he decided he had to try and take a chance.

Standing from his seat, Dean walked toward the bar and suavely took a seat on the stool next to her.  Blue eyes glanced up and smiled, and Dean’s stomach did a flip.  She was absolutely gorgeous, even more so up close.  Her makeup was perfect, and her lips were full and pouty.

“Hi. My name is Dean.” he smiled softly.

She smiled again and simply said, “Cassie.”

Dean’s smile broadened, momentarily biting into his lower lip. “Beautiful name.  Unusual.  May I buy you another wine?”

Cassie looked a little surprised but blushed lightly, “Yes, I guess you can.”

They sat for quite a while that night and talked about a variety of subjects; music, movies, books… they had very similar tastes and even where they differed drew a piqued interest to Dean.  She had a very open and unique view on the world, and he liked that in a woman. 

After finishing her second glass of wine, Cassie reluctantly stood up. “I really have to get home. It was a pleasure, Dean.”

Dean could not let this beauty walk out of his life.  He stood as well and smiled.  “Cassie, will you let me take you to dinner some night?”

Cassie looked concerned. “I don’t usually go out with men I meet in a bar, Dean.”

Dean took her hand. “Come on, Cassie.  You already know a lot about me.  Give me a chance, Please?”

Cassie looked at him for a moment as she stewed over going against her before mentioned rule, then gave into the pretty boy smirk Dean was laying on hard. “Okay, Dean.  Dinner.”

Dean smiled brightly.  For once, he felt he may have found a woman worth the effort of wooing.  The prospect of seeing her in bed didn’t hurt his imagination, either.  He then piped up, “Give me your phone number?”

Cassie chuckled softly, then rattled off her number while Dean put it in his phone.

He walked her outside as it was a dark, quiet night and spoke softly as he turned to face her, “I’ll text you and we’ll find a night.  I’m really happy we met.”

Cassie smiled at him. He definitely was a charmer, wasn’t he? “Yes, Dean, so am I.  Text me tomorrow, and I will let you know when I am free.”

And then without much more being said, she turned and walked off into the night.

 

Dean lay in bed that night and thought about Cassie.  She was just breathtakingly beautiful, and from the brief conversation they had had, she was very intelligent.  He hadn’t met anyone in a long time that he felt so comfortable with. His mind rolled around then, planning the perfect date for such an interesting yet calm and laid back lady.  Everything had to be perfect because Dean not only wanted to show her a good time, but he also wanted Cassie to have the need to call him again and want to see him again. 

Smiling, confidence began to set in and Dean rolled over in his empty bed, sighing with a feeling of accomplishment for the first time in a long time, allowing himself finally to catch some much needed sleep before work the next day.

  
  


Cassie couldn’t believe she had agreed to a date.  She was so nervous.  The conversation at the bar left a good taste in her mouth about Dean, and she decided that she liked him.  The only thing that had Cassie feeling a little uneasy was the fact that she hadn’t dated in a long time.  She mentally reminded herself that it was just one date, they were not going to get married.  Then once she saw the perfect opportunity, she would make some kind of an excuse and let Dean down easily.  

 

Cassie had been used to being single for so long, she just did not need the complications of a relationship in her life right now.  Once you were in a relationship, you had to work to make it stay strong, you had to sacrifice part of who you were to mix with someone else, you had to bend in ways you never knew possible to make sure that they felt they were wanted and needed, when all she really needed and wanted herself right now was to be happy with herself.  Sighing heavily, she rolled onto her back and stared at the ceiling, forcing her eyes closed so that she could attempt getting some sort of rest for the coming day.  This was just too much. 

  
  


Dean texted Cassie the next day:

**_Hey it’s Dean. I was thinking if you like Italian, I could take you to Vitorrio’s on Friday?_ **

Cassie picked up her phone to see who had messaged her, then smiled.  Italian was one of her favorites.  He had a good memory. 

**_I love Italian, Dean. That would be wonderful._ **

Dean’s chest was a flutter as he waited for the response, and as soon as he saw her reply, he texted back immediately. 

**_Fantastic. Text me your address and I’ll pick you up at seven._ **

Cassie shook her head with another sigh.  She was completely exhausted from her night of worrying and stressing out of an impending dish of pasta, then typed out her address, pausing before she hit send to remind herself one last time that this wasn’t forever.  And then she pressed that green button on the screen and sealed the deal.  Dean would be picking her up Friday at seven to go eat Italian.

  
  


Dean was very excited about the upcoming date.  He really wanted to get to know Cassie better.  She was already more interesting than most of the women he had met in the past.  Hell, she was the  _ most _ interesting woman he had ever met. He was really looking forward to Friday, and for the next few days, he wouldn’t be able to do much more than think about and prepare for that date, counting down the hours mentally in his head.  There was just something about Cassie that was different, he could feel it.  And his gut instincts usually never steered him wrong. 

–

Cassie was growing more nervous the closer Friday crept up, but she noticed somehow she was growing more excited.  Dean really was a sweet and great guy, or at least he seemed like that.  She couldn’t remember the last time she had a real date that did not involve sloppy drunken chat and roaming hands in a bar.  She tended to keep to herself most of the time, it was just easier that way.  But Dean made her see things much differently through his enthusiasm and obvious interest.  She was beginning to realize that she was entitled to having a little fun sometimes, and hell, it was going to be free food, right? Why not!  Walking to her closet, she began sifting through her clothing to find what would be best suited for a night at a decent restaurant with pasta, wine and good conversation.  Cassie started to plan her outfit, tossing all prospective candidates onto her bed while humming to herself softly with a smile.

  
  


Dean knocked on Cassie’s door at the stroke of seven.  He slipped a hand through his hair to make sure it looked decent, only having to wait a moment before the door opened.  Cassie looked absolutely amazing in a nice mid-thigh length black dress that clung to her hips just right with black hose and simple black heels.  The dress rested beautifully across her shoulders, and a short string of pearls drew Dean’s eyes to her chest where the neckline revealed just a touch of her breasts. Dean quickly pulled them away rather reluctantly to see the dainty pearl earrings framing her face.  

“You look stunning, Cassie.” Dean smiled.  Cassie blushed just a little.  Her eyes raked over him as well, and he happened to be in a pair of jeans with a nice blazer that covered a white button down shirt, tucked into his belt with the first few buttons left open to expose part of his chest as well.  

“You look good yourself, very handsome.”  Cassie winked, clutching her black handbag to her tummy.  Dean was amused by her reaction. Without much more to be said, he extended his arm for her to wrap around and guided her to his car.

The shiney black 1967 Chevrolet Impala sat silently in all her glory at the street waiting for them to return.  Dean walked Cassie to the passenger side, opening the door for her and closed it as she slid in.  After Cassie was seated, Dean jogged quickly around the lengthy nose of the Impala and tugged the heavy driver side door open to slide in behind the wheel, stuffing the keys into the ignition to  fire her up into a roar.

“This is a beautiful car, Dean. It’s an Impala, yes?”  Cassie was glancing around the interior of the car, getting a feel for the vintage bench seats and tan leather that laid out around them.  Even the stereo and dash were in pristine shape. 

Dean was very impressed with her knowledge of his lady in black. ‘Yeah, it’s a ’67. She’s my Baby.”

Cassie smiled.  Dean’s face had lit up when they spoke about the car, and to see such passion in a man’s eyes was absolutely astounding to witness.  Dean drove them to the restaurant with idle chit chat about cars and music.

  
  


At the restaurant, Cassie took a small sip of her wine while they sat in the booth by the back corner.   Dean was manning his beer, waiting for the food to arrive and glanced up to look at the beautiful woman across from him with a smile. 

“So Dean, what do you do for a living?” Cassie set her glass down, meeting his eyes with curiosity.  Dean smiled softer, and leaned back into his seat at the booth, toying with the rim of his beer bottle lightly with his middle finger. 

“I own Winchester Classic Car Restorations.”  Any talk about  _ cars _ put Dean at ease.  Even if it were a simple question such as this.  Cassie smiled at Dean, nodding softly as she rest her hands into her lap with her napkin.

“Oh! I know about that.  A friend of mine had his car restored with you, I believe it was a… Stingray?”  Cassie was not sure, but that was about all the details she had for him. 

“Stingray… What was his name?  I’ve restored a few of those.”  Dean leaned back toward the table, and the waitress came through, delivering their plates of food.  Dean nodded in thanks, and prepared himself to get ready to eat, glancing across the table to watch Cassie do the same. 

Cassie got a little uncomfortable. “Oh it doesn’t matter. He was pleased though.”

Dean frowned a little, but then put another smile on, grabbing a fork.  “Well, I am happy he was pleased.  I love hearing the customers are pleased.”  Cassie smiled at Dean as he spoke, and began to eat her pasta in a proper fashion, trying not to look like a slob.  

“So, what about you?  What do you do?”  Dean took a large bite after he asked, wiping his mouth and setting the napkin on the table in a ball.  Cassie glanced down, toying with her pasta for a moment of silence before she replied.  

“I write.” Cassie knew it wasn’t anything as talented or spectacular as restoring old cars or being a lawyer or a celebrity or anything, but she enjoyed what she did. 

“Wow,” Dean looked amused, “an author? That’s pretty exciting.”

Cassie grimaced.  “Not really an author. I write for blogs. I am working on a novel but it’s far from done.”

“Oh…” Dean still seemed interested regardless.  He did not have the patience to write.  “What blogs do you write for, or, what do you write about? Maybe I’ve read some of them.”  Dean took another bite, chasing it down with some of his beer while he left Cassie to answer his piqued questions.

Cassie cut quick to answer Dean, “Oh I doubt it. They’re mostly concerned with, well… certain lifestyles. Very technical and dry.” She forced a small smile, then nervously began to eat her food a bit less elegantly than she started, wiping her own chin when she felt a noodle slap down and hang from her recklessness. Dean didn’t argue with her, but he was still interested.  He continued to eat as well, and the remainder of their meal was just small chit chat about the weather and things they had watched on Netflix lately.  The food was delicious.  Dean told her about his brother who was in college to be a lawyer. He was the only real family Dean had.  Cassie said that her entire family was dead, it was just her.

“I’m really sorry, Cassie.”  Dean spoke softly, pushing his empty plate to the edge of the table for the waitress to take.  He was on his third beer, but he was in no way buzzed even the slightest.

Cassie nodded, then shrugged her shoulders and retorted a simply, “Oh don’t be. It was all a long time ago.”

Once again, Dean nodded and did not raise a fight.  He knew there was much more to this woman than she was letting on, but for now he was going to allow her the privacy she needed.  They just met each other, after all.

 

After dinner, they sat and talked over coffee.  They seemed to get along very well, their conversation was easy and enjoyable, but it was getting late.

Dean and Cassie walked slowly to the car, his hand resting in the small of her back.  The drive home was quiet, and Dean tried to surmise rather or not he had blown it by measure of her lack in interest in conversing.  Cassie was a bit uncomfortable knowing that there were many things Dean had interest in that she was just sure he would never understand.  This made her very quiet, and now she was worried she had bored the man driving her back home.  

Once they arrived outside of Cassie’s place, they sat in the car for a few minutes. 

“I really enjoyed having dinner with you, Cassie.” Dean glanced over, smiling.  She was so beautiful.  Even in the darkness of the night, the way the street lights glimmered in those large eyes made him want to lean in and kiss her goodnight.  “I would really like to see you again.”

Cassie hesitated.  She really liked Dean but she had sworn to herself she wouldn’t let this go any further than  _ one _ date.  It was that promise that even made this one date possible without her bringing a bag to hyperventilate in.  But then to her own surprise, she caught herself accepting his offer yet again.

“Yes, Dean, I’d like that.”  She nervously smiled, clutching her purse tightly to her abdomen.

They made a date for the following Saturday.  Again, Dean told Cassie that he’d text her the time and place once he decided where.  He resisted every urge inside him that wanted to kiss her, because she had seemed to be a bit on edge, and the last thing he wanted to do was spook her and lose his chance to further this– whatever it was.  

Cassie got out of the car, pushing the heavy door shut and walked up the walkway to the entrance of her home, and Dean watched her from the moment she turned to the moment she vanished behind the door, grinning to himself.  The Impala roared to life again, and Dean pulled back onto the road to head home.  Sam was about to get an earful once they spoke on the phone again. 

  
  


Once inside, Cassie walked straight to the bedroom, kicking her heels off by the door and dropping her purse onto a chair.  She then pulled her dress over her head and hung it up.  Slipping out of her bra with a sigh, she flopped down on the edge of her bed and rolled her pantyhose down and off, tossing them into the hamper.  Standing, her panties were pushed down off of her hips to fall to her ankles, and she leaned forward, reaching between her thighs to untape her cock and balls from being tucked away.  A major sigh of relief was exhaled, and she made her way to the bathroom. 

Once she stepped into the bathroom, she began her ritual of taking off her makeup, but in the middle of doing so, she began to cry.  Glancing at herself in the mirror, all she could see is the man she did not want to be, regardless of passing as the woman she wished she was with this man that had taken her out for pasta. Whenever a man came into her life it had always ended badly and she really liked Dean.  She knew for her own safety and sanity she should break it off, but she just wanted to have someone in her life for once.  She wanted to be loved and treated like the woman she was by the man she adored.   

After she finished cleaning her face off, she gave herself her hormone shot and crawled into bed.

The idea of a man interested in her scared the ever loving shit out of her, but she hoped that it was time for a  _ change…  _

 


	2. Chapter 2

The next morning, Cassie got on her computer and went to facebook to open a group chat with her two best friends Meg and Balthazar.  Meg was another Male to Female (MTF)  transgender that Cassie had been best friends with for years, and Balthazar was a flamboyant gay man that Cassie had met at a gay bar years back, and was very close to.

Cassie told both of them about Dean and the cute little date he had taken her on.  The good thing about her friends, is that they knew her so well at this point that she had no need to express her fears about this situation.  This put her at much ease while speaking to them about her life and major events in it. 

**_Meg:_ ** _ Honey, don’t count him out yet. He might be a better man than you think. He might accept you. _

**_Balth:_ ** _ That’s right. There are men out there who aren’t going to beat you up, after all. _

Cassie sighed.  She really wanted to believe everything they were telling her, but her experiences told a much different story.  

**_Cassie:_ ** _ Yeah, but you know how all the men treated me in the past, and I am not sure I can go through that again, it’s probably just best I stay single, focus on work and whatnot. _

**_Meg:_ ** _ Cassie, stop. You can’t judge every man by the bad ones. There are good ones out there! Give him a chance. _

**_Balth:_ ** _ You deserve love, babe. It’s out there somewhere and maybe he is the one. If you never give him a chance, you’ll never know. _

After a few more minutes of chatting, Cassie told her friends goodbye and logged off.  All of this talking about and thinking of being in another relationship, hell even the  _ prospect _ of another relationship made her chest hurt.

  
  


Dean couldn’t help himself from grinning like a fool at work all day, even when he was elbows deep inside the engine bay of an old car.  This stirred some curiosity within his uncle, who decided to walk up and prod at his nephew to find out what was going on. 

“Son, I haven’t seen you grin like that in quite a while, you meet a pretty girl or somethin?” Bobby leaned against the fender of the car, watching Dean pull at the wrench which was tightening a pulley. 

“I met a gorgeous woman, Bobby.” Dean stood from his hunched position once he felt safe the pulley was right, and grabbed the rag from his back pocket of his coveralls to wipe his greasy hands clean of excess grease and oil.  

Bobby grinned. “Really? That’s great, boy. I bet she’s real gorgeous, knowing you.” he chuckled.  Dean was a charmer, it was in his blood.  There wasn’t a Winchester that attracted a woman that needed a bag over her head, that was for sure. 

Dean laughed as well. “Yeah, she’s really stunning.   Her eyes are like large, blue, oceans that you could get lost in.  And her smile… But she’s also funny and smart, and very sweet.” Dean shoved the rag down into the corner of his back pocket again, grabbing the edge of the hood to use for balance as he rest his other hand on his hip, blushing. 

Bobby looked at Dean’s boyish expression, remembering that exact face so many times before as he grew up, but this time felt different.  This wasn’t just a crush, and Bobby knew it.  “Sounds like you really like this one.”

“Yeah, Bobby, I really do.” Dean nodded, biting his lower lip as he thought about Cassie.  “And her name is Cassie Novak… God even saying her name makes me happy.” Dean grinned wide, rubbing at his nose nervously by habit.  Bobby chuckled, walking over to pat the boy on the back and headed toward the office, leaving Dean alone to think about how beautiful she really was.  Words really didn’t do justice to how beautiful she was to Dean.  

 

**Hi! It’s Dean. I was thinking we could go to a club on Saturday. What do you think?**

Cassie smiled as she checked her messages and saw  _ Dean Winchester _ in the notifications.  Just seeing his name in her phone made her stomach flip.  She quickly replied;

**_Cassie: That sounds wonderful. What time?_ **

**Dean: I was thinking I’d pick you up at 9?**

**_Cassie: Sounds perfect. See you then._ **

Feeling brave, Dean sent a heart emoticon.

Cassie smiled when she saw it, but her stomach clenched and she began to worry even more.  Was it too soon to accept something as simple as a little cartoon heart?

  
  


Getting ready for the date was a trial for Cassie.  She was going to have to use tape this time in addition to tucking.  Usually she just tucked herself up and used a very tight girdle to keep things in place.  But if Dean was taking her to a club it probably meant dancing, and when dancing, things could slip loose.  Cassie couldn’t take any chances on things slipping this early in their friendship, thus, she was going to make everything as secure as utterly possible, regardless of how uncomfortable it would be to start.

Tucking was a process and took time, trial and error to get right.  Finally, once she felt everything was just right, she was ready to get dressed. 

Her dress of choice tonight had a loose flowing skirt, was a deep blue that made her eyes stand out and was one of her favorites.  The dress was more revealing in the chest than the little black dress she wore for Dean previous, so she put on a strapless bra that pushed things up and made her breasts look fuller and perkier, then slipped on some blue hose and some comfortable black heels to complete the outfit. 

Cassie really wanted to look great for Dean, so she took time with her makeup.  Even though she was determined that this would be their last date, it mattered to her that everything be perfect, as she was not one to half-ass things, especially when it came to spending time with a handsome man.

There was a knock on Cassie’s door, and she finished up the last  touches to her hair and makeup.  Taking one last look in her full length mirror, she quickly made her way into the living room to answer the door. 

Dean stood silently in place as the door opened, smiling.  He yet again, looked absolutely fantastic in a Henley that matched his green eyes and tight button fly jeans.  He glanced up and down, taking in how gorgeous Cassie looked in her blue dress which fit her like a glove in all the right places. 

“You look amazing, Cassie.” Dean had to do a double take, clearing his throat, and extended his arm out to offer his hand, in which Cassie took after she grabbed her purse and wrap from the chair by the front door.  

“Thank you, Dean.” Cassie smiled.  Thankfully, her makeup hid the burning flesh of her cheeks from his sight, leaving her to appear more collected than his red freckled face left him. 

  
  


The club was fun.  The music wasn’t so loud that they couldn’t talk, and they sat in a booth in a dark corner to enjoy one another’s company with a few drinks.  Just like before, they chatted easily.  Cassie realized that she was beginning to feel very comfortable with Dean, much more comfortable than she had felt with anyone in years. 

They spent quite a while dancing, enjoying one another’s company, laughing and chatting about the music that was played.  When the music slowed, Dean held her close to his body, wrapping his arms around her waist and she slipped her arms around his neck.  Cassie laid her head on his shoulder after a while, and her mind got lost in the feeling and the music.  She wished they could stay like this forever, but she knew it would never happen, it just was not in her future to keep something so sweet and happy in her life.

***

It was late, and they decided it was time to head home.  Returning to the Impala, they settled in, laughing at the fun they had during the date and headed to Cassie’s apartment.  

Cassie really had a wonderful time dancing with and getting to know Dean better, but her stomach was in knots knowing this couldn’t continue beyond this point. She had to break this off tonight before her feelings for Dean grew any larger, and the mere thought of them ending whatever this was made it severely difficult for her not to just breakdown right there in the car.  In turn, Cassie was pretty silent for most of the ride home.  It was the only way she could choke back the sorrow of the inevitable.

When they arrived, Dean walked Cassie to her door, and they stood for a moment in silence before Cassie unlocked it and turned back quickly to face Dean.  Dean  grabbed her around the waist  and pulled her into a kiss, resting his palm against her cheek.  At first, Cassie resisted, but then she ignored the knot in her stomach and just gave to his affections, melting into Dean’s body.  Their tongues slid together as they opened their mouths to deepen the kiss, and began to rummage around to explore one another on a more intimate level.  Cassie’s cock grew hard from the intimate embrace, and the longer they kissed the harder it grew, and the more it hurt.  The more her erection pressed against the tape that held her tucked away, the more anxious Cassie became, and suddenly she broke the kiss, pulling away with a slight gasped groan.  

“Stop, Dean, please.”  Cassie was almost breathless in her request, looking down and away, turning toward the door rather embarrassed and upset that she would have to stop their little makeout session sooner than she wanted.  

“What’s wrong, Cassie?” Dean’s voice was husky and his face was grimaced with confusion from the abrupt ending to the kiss. 

Cassie sighed sadly, pressing her fingertips to her soft swollen lips. “I… I can’t see you anymore, Dean. I’m sorry.”  Her voice sounded sorrowful as much as it did scared.

“Why?! Tell me why!” Dean plead.  He was not going to let this woman slip through his fingers as easily as she fell into his lap.  He felt like there was something here, something much more than a casual fuck.

“I just can’t… please, Dean… let me go.” Cassie turned her back to him, reaching out to turn the knob to go into her apartment, but Dean reached out and gripped her wrist, tugging her around to face him again, refusing to let her just walk away like this. 

“No! I won’t let you go, Cassie. I need a reason. You can’t just say that and not give me a reason.”  Dean’s voice had grown to desperation, and his face still furrowed a brow with his agitation in not knowing what exactly happened to change everything.  It seemed like everything had been going so well, and now it had to end? 

Cassie struggled slightly, trying to free her wrist from Dean’s grip, but he refused to allow her to slip free.  Giving in finally, Cassie heaved a sigh and threw her hands up in defeat. 

“Ok, ok! Let’s go inside, Dean. We don’t need to be putting on a show for my neighbors.”  There was a faint hint at tears growing in her eyes, and Cassie turned, opening the door to allow him inside, then she quickly shut and locked it as if what would be said inside would be intruded upon by nosey neighbours.

Slowly, Cassie walked to the couch and sat carefully, leaning forward to keep her legs together with a sigh.  Dean sat down next to her, leaning forward as well, silent.  

At least her erection had gone down so it no longer hurt.

They sat in silence until Dean spoke up softly,  reaching out to take Cassie’s hand into his own, but she pulled away.  

“Talk to me, Cassie. Tell me what’s going on with you.”  Dean’s eyes rested on her face, attempting to make eye contact any and every chance she gave him. 

Cassie was at her emotional wits end.  Turning to Dean, she replied, “I’m not who you think I am. Fuck, I’m not even  _ what _ you think I am! Dean….”  She couldn’t bring herself to say it.  This was not easy.  And every time she had tried in the past it always ended horribly.  

“What the fuck does that even mean?” Dean was staring at her with a look of confusion and anger.  This was the typical line of ending things,  _ it’s not you, it’s me. _  He would be damned if she pulled that on him, he knew what and who he wanted, and if she drug him on this far without intending to even consider anything more, he was going to be highly disappointed in himself for being so stupid. 

“Dean, I’m a male to female transgender. I was born biologically a male.” Cassie’s voice was small as a mouse, and with a red face she glanced away, then down to her lap, picking at her nails.  

There was a moment of silence, and Dean sat with a renewed look of shock, all anger washed away.

“Wait– Cassie…  are you saying you…” Dean frowned a moment, trying to actually put the puzzle pieces together, not really sure he actually believed her.   _ This has to be a ploy to push me away…. _

Cassie laughed bitterly. “Yeah, Dean. I have a cock. I’m never going to be able to be what you’re looking for.”  The tears had finally spilled over onto her cheeks, and she nervously wiped them away with her shaking palm. 

Dean just sat there, silent, his expression that of confusion yet not repulsion. He was trying to process what Cassie was saying, because he didn’t believe her, but the thought of it being true had not tugged him away from wanting to get to know her more, either. 

At last, Dean reached out once again to try and take her shaking hand, and this time she did not pull away. 

“Cassie, I don’t think I care.” Dean spoke softly, no hesitation in his voice, no tremble in his warm, strong grip around her fingers, and his eyes locked right onto her face, speaking volumes of open minded care right into her watery blue oceans that had begun to wash over onto her beautiful cheeks.  

_ Dean did not care. _

 


	3. Chapter 3

It was now Cassie’s turn to look confused.  She pulled her hand away from his hold, resting it in her lap.

“Dean, you don’t know what you’re saying. Either that or you’re a tranny chaser and that’s just…  disgusting.” Cassie looked away, wiping the runny mascara from her eyes with a sniffle.  There was  _ no way _ he even knew what he was saying. 

Dean smiled, looking down to his sweaty palms, then back over toward Cassie with a soft gaze. “I don’t even know what that means, so I guess I’m not one.” He shrugged nonchalantly. 

Cassie shook her head in pure disbelief. “No, Dean. You have no idea what you’d be getting into. This is impossible.” She swallowed hard, catching the lump in her throat, then rest her hand to her chest, trying to steady her shaking and her erratic pulse.

Dean touched her shoulder with a strong but soft grip, and Cassie turned her head to look at him through red eyes.

“When does anyone know what they’re getting into with a new relationship? All I’m saying is that I want to try.”  Dean sighed softly, then scooted a little closer, taking her hand once more, sliding his fingers between hers to interlace them, resting the other hand over the back of her palm, rubbing softly with his thumb idly.  “I really like you, Cassie.  And…  it has nothing to do with your crotch.  You’re smart and funny and just…” He smiled and half chuckled, then added,  “... adorable. I’m saying I want for us to try.”

Cassie was at a loss for words, confusion setting in.  On the one hand, she really liked Dean and wanted to continue to see him.  But on the other hand, she had a bad track record and really didn’t want to get her heart broken yet again, or even worse, anymore physical injury than she had already endured as it was.  Tears boiled in her eyes, and once again started to streak down her cheeks.  Cassie was trembling, and Dean reached tenderly to wipe them away with his thumb.

“Don’t cry. Please, don’t cry.  Just give me the benefit of the doubt here. I guess I’m asking you to take a chance on me.” Dean plead softly.  His eyes fell heavy with concern, and his heart clenched in his chest as he watched this beautiful woman cry. 

Cassie was completely overwhelmed at that point between having come out to Dean as being transgendered and then the icing on the cake– Dean wasn’t turned away or a judgemental monster.  Cassie was unable to speak, so she simply nodded and fell into Dean, her head lying upon his shoulder and she began to sob helplessly.  Dean wrapped his arms around her tight, and made soothing sounds into her ear, reaching up to hold the back of her head as she buried her face into his neck, stroking her hair.

After a moment, Cassie was able to contain her emotions and lifted her head from Dean’s neck, sniffling. “I’m ruining your shirt.” She chuckled lightly, although she felt bad for getting her makeup all over it.  Dean chuckled with her, looking into her eyes as she faced him again. 

“I don’t care.  It’s just a shirt.  It can be washed.” Dean lifted his hand to gently caress Cassie’s soft cheek, showing her that he really meant what he had told her.  Cassie blushed then smiled.  Standing from the couch, she straightened her dress out over her thighs and made her way to the bathroom to get some Kleenex to wipe her now, messy face.   She was absolutely mortified to have broken down and cried like that in front of him.  And her face looked atrocious with all the runny mascara and smudged lipstick.  She did what she could to touch up, freshening her eyes up to look more presentable.

Dean waited a moment, his mind rolling through what just happened.  

_ Man, woman, whatever, she’s absolutely amazing… I can’t fuck this up.  _

Dean not only accepted, but he was rather curious as well, wanting to know more, and he knew the best way to get to know more was to console her and let her gain his trust.  He stood from the couch and followed her quietly to her bathroom, and since the door was open, he stepped in to look at her in the mirror, his eyes making contact in the reflection with hers.  They were quiet for a moment, then Cassie turned to face Dean, and he reached out to place his hands on either side of her face, and pulled her in for a gentle, yet determined kiss.

“I’m taking you out to lunch tomorrow, and how about a movie? I’ll let you pick.”  Dean spoke intimately between them, resting his forehead against hers, his thumbs idly rubbing over her cheekbones while keeping her face in a warm embrace with his large hands.  

Cassie laughed with a warm smile, slipping her hands up to smoothe out his collar and his shirt down his upper torso, then replied with a nod, “Yes, Dean. I’d love that.”

“Good. I’ll pick you up at noon. Good night, Cassie. Sweet dreams.” Dean smiled softly, kissing her forehead, then reluctantly pulled away, his hands falling slowly to his sides, walking out of the bathroom to leave.  

Somehow, some way, all of Cassie’s fears that evening had been washed away, and she felt for once in her  life that maybe she had a fighting chance at happiness.  This thought caused her to smile wide to herself, and she turned to look into the mirror, not seeing a man dressed in drag who tucked to pass as the woman he wished he was, but she finally saw a woman that was worthy to be loved, pampered and treated like the Queen she knew she was destined to be.  Cassie went to bed that night with a smile on her face and butterflies in her stomach.  

  
  


The next morning, Cassie logged back onto Facebook and messaged her friends, telling them all about what had happened the night before. They were both thrilled to hear that they were not only right in advising her to give Dean a fighting chance, but they were extremely hopeful that Dean was going to live up to what he said to her, and give Cassie everything she needed and deserved.

  
  


Dean arrived right on time, as always, and Cassie was ready for him. She was dressed more casual this time, choosing some snug fit jeans and a peasant blouse that really showed off her breasts.  Dean was highly impressed, and told her she looked good enough to eat, which turned her face red as a rose. 

Lunch was very relaxed.  They talked about their jobs, and Cassie admitted to Dean that the blogs she wrote for were about trans problems and transitioning, and Dean actually seemed genuinely interested.  Every passing moment Cassie felt closer, as if she were able to trust him just that much more. 

Arriving at the theater, Cassie chose a superhero film for them to watch.  Dean was absolutely relieved, naturally he was sort of concerned she’d choose chick flick, but watching men run around in tights blowing things up and playing bad guys with some comedic relief tied in was much more his speed.  

They started out sitting next to one another holding hands, and then soon Dean put his arm around her shoulders and she laid her head on his.  It felt really nice for both of them.  Cassie’s mind was less on the movie, but more on wondering how good this was, and how true it would remain.  She had to talk herself out of anxiety a couple of times, and others she focused her attention on the movie so that her mind would shift away from her worry, and focus on reality– and reality was  _ good _ .

  
  


After the movie, Dean and Cassie headed back to her apartment.  This time, instead of a goodnight kiss and drop off, Dean was welcomed inside warmly, and she went to the kitchen to get them both a cup of coffee.  They sat on the couch together, just as the night before, but this time it was relaxed, comfortable.  Dean reached over and pulled Cassie closer to him, then set both of their coffee mugs down on the table, pulling her face in for a passionate kiss.  

“Stop. Please, Dean.”  Cassie objected as she pulled back, looking away.  She was blushing again, but still felt uncomfortable.

Dean furrowed his brow, confused. “What’s the matter, Cassie? Tell me.”  He felt like they had made so much progress since the night before, but had just fallen back three steps. 

Cassie blushed more, biting into her lower lip as she covered her mouth, glancing downward at the carpet. “It’s embarrassing.”

“Tell me anyway.”  Dean was persistent, and he was not going to let her push him away now, not after all they went through the night before.

Cassie took a deep, unsteady breath, then dropped her hand, glancing at the carpet at Dean’s feet, but not his face. “Well, when I go out, I tuck.”

Dean looked quizzical. 

Cassie glanced up, catching the further confusion in the man’s face.  “It means– that I tuck my genitals back so they don’t show.  You know, to appear more like…” She paused, super embarrassed, then sucked in a deep breath and continued.  “It’s fine unless I… well… unless I start to get hard. Then it hurts.”

Dean lifted both brows then, realizing what she was getting at.  It made Dean smile, and with a sigh of relief, he kissed her lips softly. “Then for fuck’s sake, Cassie, go un-tuck!”

Cassie was caught off guard, kissing Dean back softly, and blushed even more. “But Dean, it’s really  _ embarrassing _ . I mean, an  _ erection _ is embarrassing.”

Dean shifted from his playful grin to a more serious facade, then took her face in his hands. “Babe, if we’re going to have any kind of relationship at all, I’m pretty sure we’ll have sex. And I’ll see you then. I’m not into sex in the dark.” His eyes searched hers, hoping that she understood where he came from.  He didn’t know the first thing about being transgender, but he did know that this wasn’t going to sway him either way. 

Cassie sighed, and thought about everything for a moment.  Shifting her gaze back to Dean, she nodded and stood, making her way to the bathroom, and took her time to untuck.  It was a true relief to get the tape off of her groin as well as let herself hang free and breathe.  She then went to her bedroom and shimmied out of the tight jeans and blouse, pulling on some sweatpants and a fitting t-shirt.

She came back and sat down next to Dean.  Being this open around a stranger made her feel wildly uncomfortable.  Dean noticed,  but instead of pointing it out, he leaned in and kissed her again, which helped Cassie to relax.  Dean slid his tongue into her mouth and played with hers teasingly, drawn out and slow.  He ran his teeth along her bottom lip, and she moaned quietly.  Dean knew what he was doing, and it helped Cassie relax even more, knowing that she didn’t have to teach or lead him into what she liked or needed.  Her cock was pushing against her sweats to form a prominent tent, and she wiggled, trying to move and adjust herself so that it wasn’t as obvious. 

“Let it go, baby. Just forget it.” Dean knew exactly what was wrong.

Cassie nodded, and they kissed for quite a while, until they were both breathless.  Dean wanted more but he knew it was too soon, as he himself had grown a bit hard against his tight jeans. 

“I think I should go home. When can I see you again?” Dean pulled back from the embrace, and looked directly into Cassie’s eyes, licking his lips from the delicious kisses. 

Cassie thought about it for a moment, then came up with an idea for them to have dinner.  A date at  _ her _ place, and not public.  A step closer to becoming more intimate, she figured.  

“Can you come over for dinner? How about Wednesday?” Cassie searched Dean’s face for any hesitation.  With her history, this was something she had learned was imperative before taking another step in romance. 

Dean grinned broadly, and without  _ any _ hesitation, he pursed his lips. “You cook? That’s fantastic. I’d love to come over for dinner.”  

They both worked out a good time, and Dean kissed her one more time before going home.

  
  


The next day, Cassie told Balth and Meg all about what had happened. They were more enthusiastic about Dean than ever before, and wanted every detail down to how he smelled.  That meant a lot to Cassie, and she couldn’t help but blush when she was asked so many personal questions.  This was the  _ first _ time her friends had the chance to ask her about a man that actually gave her hope and self confidence.  

She shopped for dinner, planning to make a nice, home-cooked meal for Dean, and decided on her special meatloaf recipe she had been making for years that everyone loved.  Gathering the ingredients, she also grabbed some potatoes to make homemade mashed potatoes and some fresh broccoli as well. It was such a simple meal, but she really hoped it would please him.

  
  


Everything was coming along nicely as she prepared dinner, then Dean knocked on the door.  Quickly, Cassie shuffled across the living room and answered it, and Dean swept in to grab her for a kiss.  After a momentary lip-lock, Dean pulled back and took her in for a moment with a shocked surprise.  She was wearing a loose-fitting caftan– not form fitting bottoms that would require her being tucked away. 

“You untucked?” Dean asked curiously, beginning a broad grin. 

Cassie blushed and pulled back with a chuckle, a bit embarrassed at the inquiry. “Dean! You’re pushy. And yes, I am untucked.”  Admitting that was like admitting you weren’t wearing underwear for no apparent reason at all other than to make it public knowledge.

Dean smiled.  He did not intend to make her uncomfortable, it just excited him that she was becoming more comfortable around him.  “Good girl.  And man, something smells wonderful.”  Dean grinned, following Cassie as she rolled her eyes and made her way for the kitchen.

 

Dean and Cassie chatted over small things they had done that day as she finished up and served the plates up for dinner.  They sat down to eat, and Dean moaned his way through the entire meal.  Simple was good.  Homemade was delicious.  Dean not having to cook, was Heaven.  He praised her choice of entree and ate everything in sight.  Cassie was very amused.

After dinner, Dean helped Cassie clear the table, but Cassie decided they should just forget the dishes, she would do them later.  She would rather relax and spend more time getting to know Dean without her elbows deep in soapy water and food.

Cassie instead took Dean’s hand and lead him to the couch.  They got comfortable and settled, and began to kiss.  After a little bit of deep kissing, neck suckling and gentle caressing, Dean leaned back and pulled Cassie on top of him.  Cassie took the pull, and rested atop of him, and Dean could feel her erection plain as day against his thigh, but he just ignored it.  Dean ran his hands down her back, and Cassie wrapped her arms around his neck.  Dean’s lips moved down her neck and made their way to the top of her breasts, one of his hands shifting down to cup and squeeze the plump flesh, nibbling at her soft skin.

Cassie moaned from the attention to her breast, but she was scared.  Dean  _ said _ he was ok with her body, but had he ever even been with a male sexually before?  Not that she saw herself as a gay man, but a penis was not a vagina.  Cassie bit the bullet and decided to just be brave.  Dean’s attention felt way too good to stop now.  

 


	4. Chapter 4

Dean unbuttoned the top buttons on Cassie’s caftan slowly.  Sliding his hand in, he pulled one of her breasts free to rub softly over her hardening nipple, then his tongue lashed out, swirling around the sensitive mound.  His opened wide enough to take her nipple and some of her breast around the nipple in for a nice long, hard suck, and Cassie moaned out, pushing her chest closer to get more of her flesh into that talented mouth.  Her nipples always were very sensitive, and being on hormones even more so.

Dean pushed the top of her caftan back off of her shoulders to release the other breast, and licked at, then sucked that nipple just as hard as the first.  The man clearly had an oral fixation the way he used his tongue and seeing the way he enjoyed playing with his mouth.  He lifted his head and whispered quietly into her ear, his free hand grazing her hair on the side of her head in a caressing manner. 

“I want to make love to you, Cassie.  Please, let me?”  Dean whispered against her skin, pulling away from her breast to look into her eyes.   Cassie felt a thrill run through her body, mingled with an ounce of fear.  Something within her overlooked the fear however, and she decided she would allow herself to take a chance tonight, it was a thought she had already made before he even arrived for dinner.  

Cassie slid off of Dean’s body and stood up, taking his hand as he stood after her, and she led him to her bedroom.  Stopping them at the foot of the bed, she finished unbuttoning the rest of her caftan, and slipped it slowly off of her shoulders, allowing it to fall to the floor at her feet– leaving her now completely exposed and vulnerable to this man standing before her.  

Dean stood in front of her, blushing a tad bit to match her own cheeks, and took in the sight of her beautiful body.  Reaching out, he took a firm grip on both of her breasts, resting his forehead against hers and glanced down at her chest, squeezing them softly.  

“So beautiful…” was all Dean could whisper, then he glanced down to the white panties she was wearing.  They were trimmed in lace, and her hardened cock– untucked – left a definitive outline in the front, pressed up against her abdomen, the head peeking over the trim of the panties with a shiney glisten from the clear pre-cum that had built up from their little makeout session.  

Dean grazed one of his hands down to acknowledge this part of her body, then both hands slipped around her plump rear to hoist her up and lay her down onto the bed.  Crawling off of the bed himself, Dean removed his shirt, tossing it to the side, then began to unbutton his belt, then his jeans, letting them fall to his feet as well, kicking his boots off to step free.  Cassie propped herself up on her elbows to watch Dean strip, subconsciously licking at the corner of her lips as she did. When he was down to his boxer briefs, the outline of his own hard cock was clear, and he pulled them off, allowing his cock to spring free from it’s confines.  His cock was thick, and to Cassie, it was perfection and this made her blush darker, her own cock throbbing harder the more she imagined him inside of her. 

Dean returned to the bed, slowly crawling between her thighs, propping himself up over top of her to lean in and kiss her again.  This time, the kiss was a bit more sensual and intimate than before. Cassie moaned, feeling her cock harden even more, pushing against the soft fabric of her lacey panties.  Dean lavished kisses from her cheek to her other cheek, down her jaw to her chin, then down her neck softly.  Cassie’s hands wrapped around Dean’s back, and she dug her nails in while a heavy breathy moan escaped her lips, her body falling flush with her arousal of the intimate actions Dean was performing against her now hot flesh.  

Slow and steady, Dean moved his mouth down over of her breast, sucking and licking her nipple while his hand pinched and played lightly with the other nipple. 

“Ooohhhhhh…” Cassie moaned out, both of her nipples hardening under Dean’s torments.  She was proud of her breasts, she never got implants and the hormones had developed a rather natural shape and size which suited her frame nicely.  Some trans women were never so lucky. 

Dean’s hand trailed down over Cassie’s abdomen from her nipple to her belly button, and the moment it neared her cock, her body tensed and she let out a nervous whimper.  Dean paused, lifting his head from her breast to look her in the eyes. 

“Shhhh, Baby.  It’s going to be fine. Relax, ok?”  Dean’s voice was soft and sensual, and his body was the epitome of calm and collected, almost as if this was not a new situation to him.  After a moment with no objection, Cassie nodded and Dean smiled, shifting his weight down so that he could hook his fingers into the top of Cassie’s panties and pull them down over her hips, and discard them behind him.  

Cassie’s body trembled slightly in her inevitable fear that something would happen in a negative form now that she was completely exposed from head to toe to the man above her.  Dean wrapped his strong hand around Cassie’s cock, and softly ran his tongue over the head of Cassie’s cock, and she stared in shock without actually meaning to.  

Dean grinned, pulling back from her cock and whispered, “Do you have any lube?  I wasn’t exactly planning to … you know.” He was trying to help her realize that sex was something he wanted, but he had not come over here with the intent on fucking her that night.  

Cassie nodded, then rolled to her side to grab the bottle of lube out of the top drawer of the bedside table, and handed it to Dean.  Dean poured some in his hand and lubed up his fingers, and when Cassie spread her thighs for him, he lifted them up for better access.  Cassie bent her knees and held her legs up, watching Dean who was looking at her ass rather intently.  Licking his lips, Dean slipped a finger to her anus and pushed it against the tight ring, which forced Cassie to groan in pleasure.  His eyes stayed steady on her face to catch her pleasured reactions, then shifted down to his finger, pushing it past her entrance and knuckle deep to start, rubbing his fingertip around a bit for added sensation.

“Fuck, baby, you’re tight.” Dean whispered softly, working the finger in deeper very slow and methodically, working her up to open up for him.  

Cassie was wild by the time Dean finally grabbed the condom out of his wallet. He stopped a moment, staring at it and asked a very important question.

“You’ve been tested, right?” It was nothing personal, but Dean had his reasoning.  Cassie nodded quickly. “Well so have I. We don’t need these.” Dean tossed the condom aside, and lathered his cock up with more lube instead, positioning himself over her body once more as she wrapped her legs around his waist.   Dean pressed the head of his cock against Cassie’s asshole and, she took a deep breath, remembering to relax her body as he pushed into her. 

The burn was wonderful as her anus stretched to accommodate his girth.  It had been such a long time since Cassie had had sex that she had almost forgotten just how wonderful it felt to have a nice warm, thick cock inside of her.  Her arms wrapped around Dean’s neck tight and she dropped her head back to groan out in pleasure while his cock filled her up.

Dean was in absolute heaven.  Cassie’s ass was so hot, so silky and so tight around his cock.  He slowly pushed in all the way and then held once he bottomed out, allowing her time to relax and adjust to him.

“Holy fuck, Cas, you feel so good, baby. So tight on my cock…”  Dean’s words were laced with hitched breaths, gripping the sheets around Cassie’s shoulders as he trembled at the euphoria of being engulfed by this sexy woman beneath him. 

Cassie took a brief note of the shortening of her name, but didn’t care.  She just wanted him to move, and she told him so by way of wiggling her hips against him and moaning out the request in a pleading fashion.

Dean obliged, then pulled all the way out of her and thrust back in a little less soft than previous. They moaned at the same time from the friction created, and soon Dean established a rhythm that Cassie met in every thrust. Her cock bounced between them, twitching and throbbing from the pleasure she was receiving while they moved together. 

Cassie gasped out, “Please, Dean!… harder… faster…”

Dean tightened his abdomen and began to thrust harder into her, increasing his speed and listened to her delicious moans, 

“Oh yes, Dean… yes… Dean…” Cassie was breathing heavily as he pumped in and out of her, and her nails began to slip against his back, leaving the beginning of red trails in their wake. 

Dean lifted her thighs up against his chest, calves hanging over his shoulders and leaned against them, bending her in half.  He whispered into Cassie’s ear, “Touch yourself, Cas, I want to see you cum, and I want to feel your ass choke my cock as you cum all over your breasts...”

Cassie felt a fire wash through her body as he dirty talked into her ear, gasping.  She grabbed her cock and began to run her hand up and down the length in a steady, hard rhythm which matched Dean’s thrusting. She was getting so close…

Dean thrust in as deeply as it was physically possible with every thrust.  His balls slapped and bounced off of her ass and Cassie groaned out loudly, dropping her head back and to the side while she came, shooting strings of cum onto both of them, coating her breasts with the thick sticky fluid.  She tightened her muscles around Dean’s cock and began milking him into his own orgasm while she tried to catch a deep breath from her own.

Dean gasped loudly and threw his head back, growling out into a groan of pleasure, his hips moving in steady thrusting motions while he filled her ass with his thick warm cum. 

“Fuuuucccckkkkk!” Dean shuddered at the feeling of her tight ass around his now spent cock, slowing his hips to an almost still motion, trying to regain his own breath as he came down from his own orgasmic high as well.  It took him a moment, but when he was able to move, Dean pulled out slowly, and his cum oozed out of her contracting hole, dressing the crack of her ass as well as the bed beneath her.

Dean rolled over and rested on his back next to her, slinking an arm around her waist to pull her body closer to his.  Cassie settled her head on his shoulder, and draped her arm and thigh across his body in a very exhausted motion.

“Was it… was I… okay?”  Cassie whispered in a small voice. 

Dean turned his head to the side to face her, and looked at those beautiful eyes with a smile. “Okay? Baby, you are a beautiful woman who can’t get pregnant, never has a period and only wants anal sex. You’re a unicorn, and you’re all mine.” He smirked at that thought, and leaned in to kiss her lips softly.

Cassie giggled, returning the kiss, and blushed, burying her face back against his chest as they cuddled, for once in her life feeling like something was going right.  

 

Later, cleaned up and cuddling on Cassie’s bed, she asked Dean if he would stay the night.  

“I was planning on it, baby.” Dean spoke happily with a smile, caressing her cheek with his thumb idly.  

Cassie sighed in relief.  This was just awesome.  She never actually realized just how much she missed this.  Not just the sex, although that was amazing, but the closeness and intimacy with another person, the intimacy she had been missing for years and didn’t really even know it. 

They both fell asleep spooning.  Cassie snuggled back against Dean, and for the first time in years, she got a decent night’s sleep, smiling as she drifted off. 

 

_ Cassie was a unicorn, and Dean was not going to let her go.  _

  
  



	5. Chapter 5

Cassie woke up groggy, feeling arms wrapped around her body.  She turned over in the bed, trying not to wake Dean. He looked so peaceful in his sleep, and she smiled warmly.  It was such a wonderful sight to wake up next to a man so sweet and caring.  She lay there without saying anything for a moment, taking in his features in the morning sunlight, until he scared her by mumbling.

“Watching me sleep is a little creepy, Cas.”  Dean grinned. 

Cassie laughed and blushed.  “Then don’t look so damn sexy when you’re asleep.”

Dean rolled over and wrapped her up in his arms, making her squeal, and kissed her. 

“I want to make you breakfast, so you’re going to have to let me go, Mr. WInchester.” Cassie giggled.  Dean was kissing her all over her face and down her neck.

“Nope.” Dean held on to her, chuckling at her cute little giggles.  Man, it really had been a while since he woke up next to a beautiful woman.  Cassie wiggled trying to get loose, but Dean just would not let her go.. 

“You aren’t going anywhere. Just accept it.” Dean mumbled, kissing her on the lips again.  His kisses were sensual and sweet.  Cassie kissed him back with a soft coo of a moan, then smiled, breaking the kiss. 

“But don’t you have to go to work?”  She didn’t want the man to lose his job over some cuddles. 

“I’m the fucking boss. I can go in anytime I want to. Now kiss me, woman.”  Dean smirked, looking into her beautiful blue eyes.  Cassie caved, kissing Dean with unsurpassed passion.  It began to get a bit heated the more they kissed, and there were thoughts flying through her mind about how wonderful Dean WInchester was.  How great he treated her, how he accepted her so completely.  And for once, this was a man who had no issues with her gender transition. 

After a good long minute or two of making out, Cassie felt herself getting hard.  Dean’s cock pressed against her stomach just as hard, and then his arms gripped her tight, pulling her up against him, trapping both of their cocks together between them with a soft moan into their kiss. Dean’s hips began to grind his cock against Cassie’s, which caused Cassie to catch a breath and moan out, quivering.  Dean’s hand slipped up to her face, cupping her cheek and he deepened the kiss, almost desperately.  Cassie responded just as desperate in return. 

“Cas…” Dean moaned into Cassie’s mouth.  Cassie clung to him. It was as if time stopped and they were the only two people on earth.  Dean moved his mouth from Cassie’s as his body shifted down, and he took her nipple into his mouth instead, sucking on it vigorously. Cassie closed her eyes tightly and let herself go, allowing herself to just feel the sensations he was giving her by teasing her body.  The pull, almost but not quite painful, the grinding of her cock against his belly, and the thought of being touched,  caressed and cared for by this man drove her crazy with love and lust.  She knew she was lost.

Dean pulled away from her breast and moved down, licking at her cock. 

Cassie gasped, “No, Dean…” but he had it in his mouth already.  She whimpered, wanting it because it felt so good, but not wanting it because she was still rather uncomfortable with her male body parts being touched. Dean sucked down to the base and nuzzled his nose in her pubic hair, then sucked back up.  Cassie tried to pull him off, and he looked up at her  with slight confusion, letting her cock fall out of his mouth.

“Please, don’t Dean. Please… it’s just….” Cassie couldn’t finish, but her body screamed that she was rather uncomfortable. 

Dean moved back up and looked her in the eye. 

“Cas, it’s a part of you. An important part. I want to make you feel good is all.” Dean looked concerned.  His hand pressed against her cheek and cupped her face, caressing it with his thumb. Cassie was trying not to cry, tears were welling in her eyes. 

“Then just fuck me. Just fuck me Dean, that’s all I need.” She shook her head, rather upset at this point.  The hormones were kicking in with her panic.

“No.” Dean shook his head.  He was not about to  _ just fuck _ her.  They either made love or nothing.  Cassie looked at Dean with tears streaking down her soft  cheeks, and she trembled.  Dean’s gaze back at her was genuine affection, love, care and wanting to help her feel better.  

“We need to talk about this, Cassie. I need to understand. I need you to explain things to me so I can understand.” Dean spoke softly.  There were so many thing he did without meaning to upset her, and he didn’t want to continue.  He needed to know her limits. 

Cassie sighed. “If we’re going to talk, I need coffee.” She wiggled out from underneath him and stood up, pulling on a robe.

Dean slipped out of the bed as well, and pulled on his boxers before heading to the kitchen right on her tail.

 

Dean and Cassie sat at the kitchen table with hot mugs of coffee in front of them, Dean waited quietly, patiently for Cassie to talk. Finally, Cassie sighed,

“Dean, I hate my dick. I know it’s the only way I can really feel pleasure, but I still hate it. It isn’t  _ ME _ , you know? It isn’t supposed to be there. If just… feels wrong.” Cassie’s face showed mild disgust while talking about her body, and she looked down, embarrassed. 

Dean felt a real pang of sadness, hearing her say this.  

“But Cas, it is a part of you. You need to learn to live with it, or else get the surgery. Why haven’t you gotten the surgery anyway?” Dean was trying to understand and be supportive, to show Cassie that he liked her the way she was regardless. 

And there it was. The question they all asked.

“There’s a lot of reasons, Dean. It isn’t always successful. I know two people who have trouble pissing. Some people lose all sensation and it never returns. They can’t feel any sexual pleasure at all. It’s scary. And it costs a small fortune, just to take the risk. I’ve struggled with this all my life. I am  _ not _ going to take the risk.”

Dean nodded. He had no idea that it was that complicated, but thinking it through, it had to be. And he really didn’t want Cassie taking the chance, either.

“Babe, I understand. I really do. Hearing that, I don’t ever want you to have the surgery either. But I do want you to learn to, well, if not love your cock, at least learn to live with it. I want to be able to go down on you, to jack you off, as well as make love you. I want to experience everything with you. I care about you, Cassie. I really do.”

Tears were flowing now. Cassie sipped her coffee in an attempt to get control. Setting the mug down, she nodded.   

“I’ll try, Dean. For you, I’ll try.” She wiped at her tears, sniffling.  This was such a tough subject for her. 

Dean leaned across the table and kissed her gently. “That’s all I ask baby,”

  
  


Dean went to work, promising to text her later.  Cassie logged on to her computer and opened up a chat. Balth was there but Meg wasn’t. Cassie told Balth everything. Balth asked the occasional question, but mostly he just let her tell it. When Cassie was done, Balth spoke his mind,

“He sounds like a keeper, Cassie.” Balthazar knew there were few men in this world who would accept a woman of her caliber.  She was an outstanding woman in Balth’s eyes, one of his best friends, and for her to find a man that not only accepted her for who she was, but treated her like a real woman as well, that was a keeper. 

Cassie stopped and thought about it.  

“I agree, and I’m scared to death.” Cassie brought her hands to her mouth as she hit send, trying to still contain her emotions. 

Balth understood. He and Cassie had been friends for many years and he knew what she had been through. All the pain, the disappointments and the actual physical attacks, so typical of the trans women in this society. He just wanted the best for her.  He asked if she was going to share any of her past with Dean.  Cassie thought about it.  On the one hand, she realized it would explain a lot about her, but on the other, she didn’t want him to see her as weak or needy.  

“I’m not really sure yet.” Cassie replied.

“It will help him understand you, Cassie. Why you’re afraid.” Balth shot back. 

“I know, I know.” Cassie answered, then they both signed off shortly after.

  
  


Cassie had been working  on her blog for about an hour when her phone chimed.

**DEAN: Hey baby. I’ve been thinking about you and almost got a hard on in a meeting. I’m picking you up at six and taking you to dinner.**

Cassie smiled. 

**_CASSIE: Okay. Sounds wonderful. Dressy or casual?_ **

Immediately he responded.

**DEAN: Casual. And NO tucking!**

Cassie bit her lip.

**_CASSIE: But Dean…_ **

**DEAN: NO!**

**_CASSIE: Okay._ **

Cassie rubbed her face, unable to believe that she just agreed to go out in public without tucking.  A few moments passed and she went back to work, but it worried her.  Going out with just panties to hold her was risky.  She just hoped Dean knew what he was doing.

  
  



	6. Chapter 6

**Notes for the Chapter:**

> Sorry about the late post, but.... reasons

As usual, Dean arrived right on time. Cassie had chosen to wear a pair of tight button fly jeans and a low cut blouse. Dean glanced her over approvingly, then leaned in to kiss her lovingly. 

“I get it. It’s like being tucked, right?” Dean whispered into her ear. 

Cassie blushed and nodded.

Dean took her to his favorite burger joint.  The bacon cheeseburger was his favorite.  Dean wound up eating most of Cassie’s fries and they both drank a beer.  Dean talked about his day at work, jokingly telling her about day-dreaming about her in the meeting and his cock getting half hard.

“See what you do to me, woman? You’re making me nuts.” Dean chuckled, throwing half a fry back into the plate.

Cassie laughed.  The date was turning out to be a lot less stressful than she originally anticipated, not being able to tuck. 

After dinner, Dean took them back to his place.  Cassie had never been to his place before, and Dean felt it was time she saw where he lived and what his lifestyle was like.

 

Dean’s apartment was shockingly beautiful for a bachelor.  Everything was modern, shiny and clean.  He had very interesting art on the walls which gave his apartment some life.  There was a balcony overlooking the city. Dean lived on the eighth floor, so glancing out over the balcony was absolutely breathtaking at night. 

Dean fetched them both a glass of wine and he led Cassie out on the balcony as he handed her a glass. Cassie leaned on the railing taking in the view.

“It’s breathtaking, Dean.” Cassie said wistfully, smiling. 

Dean moved closer and said softly, “No, it’s just a view.   _ You’re _ breathtaking.”

Cassie turned toward him and smiled with a blush.  “Oh, you silver-tongued devil you.”

Dean cupped her face with his free hand and replied with a grin, “I’d love to show you what that tongue can do.”

They began to kiss, and it became hot and wet very quickly.  Dean explored Cassie’s mouth with his tongue and he sat his glass of wine down on the railing, slipping his hand over one of her breasts, cupping it with a firm squeeze.

Cassie was wearing a strapless bra, and he pulled down her blouse and the cup, putting his mouth on her breast, encasing her nipple between his lips for a firm suck.  

“Dean, not out here…” Cassie reluctantly tried to pull away, not wanting to be exposed to the public eye. 

Dean spoke against her breast, “No one can see us baby.”

Dean continued to suck on her nipple and it was getting very uncomfortable in her jeans. Cassie wiggled and whimpered a little in Dean’s grip.

Dean stood up, looking at her with his smirk. “Let’s get you out of these.” He began to unbutton her jeans.

Again, Cassie tried to protest but Dean just ignored her. He unbuttoned Cassie’s jeans and yanked them down. Kneeling, he pulled off her shoes and pulled each leg over her feet, leaving her in just her panties.

Dean then got down on his knees and rubbed over Cassie’s panty covered cock, pressing his mouth against it, sucking on her panties.  Cassie moaned and pushed her hips towards Dean’s face involuntarily. Dean sucked a wet spot into her panties over her cock, which by now was growing rather hard.

“Dean… don’t…” Cassie tried begging through panted breaths. 

Dean mumbled around her cock, “Hush, Cassie.”

Dean continued to suck on her cock through her panties, sometimes dipping down to suck on her balls. He finally reached up and hooked his fingers into the sides of her panties, pulling them down. Cassie’s cock sprung out, and Dean gripped it at the base, sucking it deep into his mouth, causing Cassie to moan outwardly louder than she intended to.  Dean took all of it in until it was pushed against the back of his throat and held it there for a moment. Cassie gasped softly and groaned. 

Dean let her slip free from his mouth and smirked. “Good girl.” 

Dean pulled Cassie’s panties all the way off and turned her towards the railing.  She grabbed it firmly and stuck her ass out for him. He had definitely gotten her worked up to the point that she had relaxed and wanted more, regardless of being eight stories in the air on a balcony. Dean shoved two fingers into Cassie’s mouth, and she sucked on them greedily.  When they were wet enough, Dean pulled them out and pushed one into Cassie’s tight hole. She gasped and clenched tightly around his intruding finger. 

Cassie was struggling to relax, and when she did, Dean pushed his finger in all the way and felt around until he found her prostate. He rubbed it steadily, and Cassie jerked.

“Oh my god, Dean…” Cassie cried out, not used to this type of pleasure being given to her by anyone other than herself. 

Dean took that opportunity to put another finger into her.  Cassie pushed back against them, and Dean moved them in and out of her, opening her up for him.

When Cassie was open enough, Dean let a long tendril of spit drop onto her hole. He grabbed his dick and rubbed it around in the spit, then pushed in slowly but firmly.

Cassie groaned out. It hurt but not for very long as it settled into the burn she loved.  Dean held still, letting her relax, then he pushed all the way into her.

Cassie completely forgot that they were outside on the balcony at that point.  She closed her eyes and pushed back against Dean’s every thrust.  He was so thick, it felt like she was being split but she loved it, craved it like oxygen. 

Dean held her hip with one hand, and spit in the other.  Reaching around, he grabbed her cock and began to run his hand up and down the shaft, rubbing his thumb over the head every swipe.  Cassie helplessly moaned and pushed back against his cock and hand back and forth as much as she could.

Dean slipped his hand from her hip to rest upon her belly, low, and held her tight as he moved in and out of her.

Cassie moaned out a long, “Deeaaan…” as Dean kissed the back of her neck.

“You feel so good on my cock, Cas. So fucking tight…” Dean huffed in a whisper against her neck and ear with a hot breath playing against her flesh. 

Increasing his speed, he began to rock his hips into her a bit harder.  Cassie groaned out his name over and over.  Dean could feel her tense around his cock by how she tightened around him.  He knew it wouldn’t be long before she had to release. 

“Cum for me baby. Cum in my hand.”  Dean coaxed her, encouraging her to let loose and just ride out the pleasure. 

Cassie nodded and breathlessly cried out, her cock twitching and then releasing heavy spurts of cum into his grip and onto the floor of the balcony.  Dean’s hand filled with her cum, and he squeezed every drop from her even as he came inside her. 

Cassie clenched and unclenched, milking his cock for every drop as she tried to catch her breath. 

Dean bent over Cassie’s back, kissing along her spine as he caught his breath.  Cassie’s knees were weak, and he pulled out of her, then pulled her back against him from the balcony railing.  He scooped her up into his arms, her legs around his hips and carried her to the bathroom.  Dean reached out with one hand to turn on the water in the huge claw foot tub, then sat down on a chair with Cassie in his lap.

Dean kissed Cassie’s face and the top of her head over and over, telling her what a good girl she was and how fantastic the sex was. 

When the tub was full, Dean slipped Cassie into the water and stripped, sliding in behind her.  He pulled her back to lean against his chest, then held her gently in a warming embrace.  Cassie sighed and relaxed into him.

Dean washed her gently, taking his time to make sure that she was clean from head to toe, inside and out.  When he cleaned her anus he was extra gentle.  Cassie shuddered against him as his fingers so gingerly removed any of his cum left inside of her he could.

When they were finished bathing, Dean got out first and pulled Cassie out effortlessly.  He wrapped a huge fluffy towel around her and picked her up again.  Cassie rested her head on his shoulder as he carried her to his bed, now feeling completely relaxed, loved and more importantly; safe to be herself.

Dean pulled them under the covers, pulling Cassie into the front of his body and they both slept soundly, spooning in a warm and loving embrace.

 


	7. Chapter 7

 

 

Dean kissed her awake. She opened her eyes and smiled at him.

“Good morning, beautiful.”

She just looked away, and said, “Good morning.”

They cuddled and kissed a bit, but then they had to get up. Dean had a meeting he had to get to, and he needed to take her home first.

When they got to her place, he pulled her to him and kissed her again.

“Listen, baby. One of my friends is having a party on Friday. I need you to go with me.”

Never thinking twice, she just said yes.

 

They didn’t see each other on Thursday. He had a lot of work to catch up on and she was behind on her blogs, so they agreed to wait until Friday, when he took her to the party.

She missed him. She chatted with Meg on the messenger. Meg was thrilled to hear about how things were going, and agreed with Balth that Dean seemed like a keeper. Cassie said she had never been happier.

 

 

Friday Cassie spent a lot of time getting ready for the party. She wanted Dean to be proud of her. She wore a very slinky purple dress that she’d never worn before. Her hair was its usual messy self but she was used to it. She tucked, of course. She wore lavender hose and purple flats. For jewelry, she chose tiny hoops in her ears and a plain gold chain.

Dean was awestruck when he picked her up. He just kept telling her how fantastic she looked and she felt proud of herself.

 

The friend’s house was opulent. He obviously had a lot of money. Servants passed around trays of appetizers and she was given a glass of white wine. Dean was talking to someone so she just leaned against a wall and looked at the people.

Then she heard a loud voice. He was telling a joke to the amusement of everyone around.

“Hey! How do you fit three homosexuals on one barstool?” He paused.  “Turn it upside-down!”

Everyone laughed. Cassie froze.

Then he said, “Get this one…  What's worst then picking up a hot blonde at the bar and having erection problems? She has one!”

Cassie saw red. She turned and heard the next one while everyone around the man was laughing.

“What's the best part of punching a transvestite in the face? You get the pleasure of punching a woman but with none of the guilt!”

She turned and ran towards the door.

Dean saw her and went after her. He grabbed her arm and was asking her what was wrong, but she just wrenched her arm away and yelled, “Let me go!”

She ran out of the door and down the street, crying.

Dean was right behind her. When he reached her, he grabbed her and held her in his arms. She struggled to get loose but he was too strong.

Dean was asking what was wrong. Cassie could barely breathe.

She gasped out, “Those… those are … your… friends? You fucker!  So you fuck me…. and laugh… at… tranny jokes… at work?”

Dean just looked at her. “What are you talking about?’

“Oh, I heard your friends. They seem to think that beating up trannys is a big joke.  So what, how many weeks do I have before you wake up one morning, decide you’re not gay and you beat the fuck out of me?”

Dean looked at her like she’d lost her mind. But then realization dawned on him.

“Wait. Cassie, did someone beat you up?”

Cassie laughed with a touch of hysteria in her voice. “Someone? Try four someones.”

Dean had a stricken look on his face.

“Baby, first of all, I’ve never heard any of my friends make jokes like that, and believe me, they never will again when I’m through with them. I would never, do you hear me, _never_ make a joke about you. What we have, who you are, is no one’s business but ours. And I would kill anyone who touched you wrong. I can’t stand the idea that anyone hit you.”

Cassie was sobbing against his chest. He picked her up and carried her to his car.

He drove to her house. She had stopped crying and was breathing normally, but she just sat with her head against the window and never said a word.

Once he got her home, he led her inside and to her bedroom. He went and got a wet cloth and wiped her face. She just laid there, He took off her dress and her hose. He just stared at the tight girdle she had one, then he pulled it off too. She rolled her face to the side and didn’t look at him.

He was appalled when he saw the tape. There was a V of tape that started in her groin on either side and led between her legs. He bent her knees and was horrified to see the duct tape that held her penis in place. He gently pulled the V of tape off her. Then he began to pull the duct tape off. Her penis was sheathed in a tube of stretchy knitted material that kept the tape off her penis. He got the tape off and pulled the tube off her.

She still just laid there not looking at him. He pulled her up in a sitting position and held her against him.

“Listen to me, Cas. I never, ever want you to do that to yourself again. Do you understand me? Never.”

She looked at him then with a sneer on her face. ‘Oh yeah? You would rather I just let it hang? Let everyone see it?”

He kissed her forehead. “No, baby, but you can just wear the girdle, it’s enough.”

She sighed and let her head droop against him.

He dug around in drawers until he came up with an oversized T shirt and put it on her.

“Now, Cassie Novak, you tell me about who beat you up and why.”

 


	8. Chapter 8

Cassie was sitting on the bed with her legs under her. Dean sat across from her.

“It’s not that unusual, Dean. Men get with a transgender woman and after sex, usually the first time but not always, they suddenly decide that having sex with us makes them gay. They freak out and beat us up. Usually while yelling that they’re not gay.”

“Jesus Fuck, baby, and this happened to you four times?”

Cassie nodded.

“The first time was in college. I was very shy and really, didn’t date. I met a guy in one of my classes and he wanted to take me out. I just thought it would be fun. I had no intention of sleeping with him. We went to dinner and then we just walked to a park. It was late. He got very pushy and I told him no, to take me home.”

Cassie looked down. “He forced me.”

Dean’s face reflected the pain he was feeling. “He raped you?”

Cassie nodded. “He hit me and I fell down. He tore off my skirt and when he saw…  well… me, he raped me and then beat the shit out of me.”

Dean wanted to kill someone. “Did you go to the police, Cassie?”

“No.” Cassie looked at him. “I didn’t want anyone to know about me, and I felt like it was my fault anyway. I never should have agreed to go out with him.”

“It wasn’t your fault, baby.”

Cassie smiled a rueful smile. “Oh I know that now. But back then, I was terrified about anyone finding out what I was.”

“Anyway, the other three were guys I was dating. They knew about me, full disclosure. But each of them just freaked one day. Started saying that they weren’t gay, and beat me up. One put me in the hospital. I had to tell the police about him, and he ended up on probation. That’s when I left town and moved here. And you,” Cassie looked at him, “are the first man I’ve dated since I moved here. It’s been four years.”

Dean sighed. He hated hearing this. He just wanted to wrap her up and protect her from everything that had ever hurt her.

“So, why me? I mean, why did you go out with me?

“Because I was attracted to you, Dean. And it had been such a long time. But I was only going to go out with you twice. Just twice and then just break it off.”

“But you didn’t. You gave me a chance.” Dean smiled at her.

Cassie looked away. “But I tried. I really did. I just… well I like you. A lot. But…”

“But what, Cas? Tell me.”

“But I’m still frightened. I’m scared that you’ll decide one day that you aren’t gay either.”

Dean took her arms and pulled her closer. “Listen to me, Cas. I don’t think of you as anything but a woman. A fully-functioning, beautiful woman. But if being with you means I’m gay, fuck, I’ll take out a full page ad in the newspaper, stating I’m gay. I don’t give a fuck.”

Cassie just stared at him.

“And as far as those cocksuckers at the party, I’ll deal with them. No one’s gonna make the woman I love feel uncomfortable.”

Cassie’s eyes got big. “Woman you _…  love_?”

Dean grinned at her. “Yeah, the woman I love. I love you, goofy.”

Cassie just looked at him. Then the tears started. She wiped them away angrily. “You’ve only known me for less than two weeks. How can you love me?”

“Because I know you’re the one, Cas. The only one for me. I’ve known since our second date.”

Cassie was sobbing now. She stuttered out, “I… I love… you too…”

He kissed her through her sobs. She settled and the tears stopped. She threw her arms around his neck and just clung to him.

 

She was exhausted. It had been a roller coaster of emotions and she was worn out. He stripped and got into bed with her. They spooned and she was asleep in minutes. It took him a lot longer. He couldn’t stop thinking about the people who had hurt her. He really felt like he could kill them if he ever met them. Finally, he drifted off.

 

Cassie woke up early in the morning, with Dean’s hard dick pressed between her legs. He was so thick, it felt so good. The head of his cock was pressing against the back of her balls. She couldn’t help herself, she began to move back and forth on it.

She bit her lip to suppress a moan. Then she heard his voice, gravely with sleep, say, “Hand me the lube.”

She fumbled around and found the bottle on the bedside table, and handed it back to him. She listened to the top pop open and then close again.

Then his finger was in her. She moaned and pushed back on it. He worked it in and out a few times and then added another finger. He worked fast, obviously as turned on as she was. Then his fingers slid out and the head of his cock was pressing against her hole.

She groaned and pushed back on it, forcing it into her. She just kept sliding back until it was fully in her. She bent her top leg and pulled back, then thrust herself on it again.

“That’s it. Baby. Use me.” His voice sent a thrill through her.

She slid back and forth, fucking herself on him. He reached around and grabbed her aching cock, running his hand up and down the shaft. His other arm was under her neck and he bend his elbow and grabbed a breast, pinching the nipple.

Cassie just rammed herself on and off him until she was gasping, “Dean… Dean I’m coming…” and she filled his hand. She clenched hard on his cock and he grabbed her belly, smearing cum all over her, and held her while he fucked her harder and faster each thrust.

“Oh Fuck…. Cas… fuck, I love you…” and he filled her. He kissed the back of her neck over and over again.

 


	9. Chapter 9

Cassie woke up feeling lighter and happier than she had in years. She was loved, truly loved, by a wonderful man. She turned her head to watch him sleep. She had to pee so she sneaked out of bed quietly and went to the bathroom. She peed and brushed her teeth.

When she went back into the bedroom he was still sleeping, so she pulled on a long T and went to make coffee. She was standing, sipping and leaning against a counter when he wandered in. He was naked and the sight took her breath away. His hair was all spiky from sleeping and he looked so sexy she felt her cock twitch.

“I woke up and you weren’t there.” He spoke in a pouty voice, scratching his head. He walked up to her and pulled her close for a long kiss.

She smiled and got him a cup of coffee.

While he sipped it, she asked what he was going to do today.

He grinned mischievously. “Well, it’s Saturday, so I planned on taking you back to bed and fucking you all day.”

She giggled.

He added, “With food breaks of course.”

“Of course.” She was beaming at him.

She finished her coffee. “But first, I’ve got to inject.”

Dean looked confused.

She just said, “My hormone injection,” and walked to the bathroom.

He trailed behind her, and stood in the doorway, watching. She got the bottle out of the medicine cabinet, and pulled a syringe out of a drawer. She got an alcohol wipe, and pulled up her T to reveal a hip. She opened the syringe package, turned the bottle upside down and drew up some of the hormones. Then she swabbed a spot on her hip, jabbed the needle in and pushed the plunger.

He watched her every move. When she opened up the cabinet under the sink and put the syringe into a red box, she turned to him and simply said, “Done.”

He asked her how often she had to do that. She replied that she injected twice a week.

“For the rest of your life?’

She nodded. “Yes, for the rest of my life.”

He just kissed her and said, “I’m sorry you have to go through that, baby.”

It was such a routine for her, she gave it very little thought anymore.

Dean followed her to the bedroom. He sat on the bed and asked her if injections were the only way for her to get hormones.

“Well, no. There are patches and they are supposed to work better with fewer side effects, but they’re really expensive.”

Dean jumped up, startling her. “Fuck that! We’re going Monday and getting you the patches.”

Cassie just looked at him with her mouth open. “Dean… I can’t let you pay…”

He cut her off. “You can and you will. I hate the idea of you having to jab yourself twice a week forever, and you said there were side effects. I need you healthy, woman.”

“Thank you, Dean.”

“Don’t thank me. I’m here to take care of you. And while I’m being all manly here, I want you to move in with me.”

“Dean, I can’t move in with you. We’ve only known each other a few weeks.”

“I told you, I knew you were the one on our second date. Hell, I’m doing my best to stop myself from proposing here.”

Cas got a stricken look on her face. “Dean, I can’t marry you. I can never get married.’

Now Dean looked stricken. “Why, Cas? Why the hell not?”

She looked at him with fire in her eyes. “Because I would have to get married using my birth name. My name is not legally changed. And I would have to get married as a male.”

Dean sat back down on the bed. He thought for a few minutes.

“Baby, a legal name change is easy. We can do that on Monday too. And as for marrying as a male, who the fuck has to know? I mean, it might say that in some dusty file somewhere, but as far as anyone would know, I was marrying the woman of my dreams.”

 

He opened his legs and pulled her to stand between them. He pulled her T over her head, leaving her standing before him nude. He took a breast in his mouth, sucking hard on her nipple. She moaned and her cock twitched.

He ran his hands over her belly and down her sides. Her dick began to fill. He moved his mouth down and took it in his mouth down to the root. Cassie groaned and tried to not thrust her hips against him. He sucked up and down while his hand lifted her balls. He ran a finger into the crack of her ass and circled her hole.

Then he popped his mouth off, grabbed her and threw her on the bed. She lay on her back and spread her legs wide for him. Growling, he pushed her legs in the air and licked a flat tongue over her hole.

“Dean? What… where did you…”

Dean lifted his head, smiling. “I knew watching all that porn would pay off someday.”

He went back to licking her. Cassie thrashed her head and moaned louder than ever before.

 

Dean ate her out like it was his last meal on earth. Cassie was begging him before he was done with her. He grabbed the lube, lubed up his fingers and pushed two into her. It didn’t take long before she was ready and he moved up over her. Pulling her legs onto his shoulders, he pushed in.

Dean slid in all the way, and then pulled back and slid in again. He felt wild with need, wanted to pound her like he never had before.  He tried to control himself but listening to her moans and feeling her push back on his every thrust, he just went hard in her.

“Make yourself cum, Cassie.” He sounded like he was ordering her but she responded and grabbed her cock, running her hand up and down fast. It was over quickly. She came all over her belly and he came deep inside her.

He just gasped out, “I love you so much…”

 


	10. Chapter 10

Dean woke up in the middle of the night and reached for Cassie but she wasn’t in bed. He listened for the sound of a toilet flushing or something similar, but when some time passed and there were no sounds at all, he got up and went to look for her.

He found her in the living room, on the floor next to the couch, crying. He pulled her up on the couch and wrapped his arms around her.

“It’s just the injection. I’m fine, go back to bed.” Cassie sniffed into his shoulder.

“Of course I’m not going back to bed.  Are you sure it’s just the hormones and nothing else is wrong?’

She put her head on his shoulder and sobbed. He held her until she quieted and then she lifted her head and looked at him.

He wiped tears off her cheeks. She sniffled. “Dean, I’m frightened all the time.”

Dean looked at her, concerned. “Frightened? Of what?’

“Of this, of us. I keep thinking that it’s going to blow up in my face, and when it does, I’ll just curl up and die. I never thought anyone would love me, and now I have this amazing man in my life and it just… it scares me.”

“Damn it, Cas. I love you and I’m always going to love you. Forever. You are the best thing that ever happened to me and nothing is ever going to change how I feel about you. Now, you are going to move in with me, do you hear me? Let me prove to you every day how I feel about you.”

Cassie just shook her head, “It’s too soon.”

Dean growled at her. “Then I’m going to text you every hour until you agree.”

They went back to bed.

 

Cassie slept later than usual. Dean got up and made coffee, and brought a cup made just the way she liked it, and sat it on the bedside table. He leaned over and began kissing her face.

Her lips curled into a smile. Without opening her eyes, she said, “Is that coffee I smell?’

“Indeed it is, my sweet.”

She sat up in bed and took a sip. ‘Ummm. I could get used to this.”

“That’s the idea.” He touched her cheek.

 

After she finished, He grinned at her and wiggled his eyebrows. “You know what I figured out while I was making coffee? That we have never showered together. Time to change that.”

 

In the shower, he pulled her to him and they kissed. But then she broke away and went to her knees. She lifted his cock and licked across the head.

“Oh fuck, Cas… “Dean looked down at her.

She sucked the head into her mouth and felt it harden. She stuck the tip of her tongue into the slit and Dean groaned. He got harder and bigger.

He was thick, really thick. It actually stretched her mouth a little trying to get it all in. She sucked on the head and then ran her lips down the shaft. Dean threw his head back against the tile. She couldn’t get all the way down on him, he was too long and she was afraid she’d gag. So she wrapped her hand around the base and just sucked up and down, licking the underside every once in awhile.

Dean was groaning loudly and had his hand on her head. He didn’t press, he just was touching her.

He was so silky and hard in her mouth, she just loved it. He tasted so good, so _Dean_. She listened to him groan and it spurred her on to move faster up and down. She twisted her hand on his root every once in a while, and then he gasped out that he was so close.

She pulled back and his hot, salty sperm filled her mouth. She struggled to swallow it all; she hadn’t done this in years. Some spilled out on her chin. She looked up at him and he had a wrecked look on his face.

“Damn, woman, you look good wearing my cum.” He pulled her back up and licked it off her chin and then stuck his tongue in her mouth. She sucked on it greedily. Their kiss was just cosmic.

They washed each other, taking their time.

 

She made breakfast and then they spent the Sunday reading the newspaper, napping, making love several times and eating. Cassie was feeling so relaxed, so comfortable and yet, that little voice in the back of her head continued to nag her.

‘ _You don’t deserve him_ ,’ it told her, ‘ _don’t get comfortable, this will never last… he’ll leave you just like all the others…_ ’ She did her best not to listen this time. Maybe this time, things will work out for her.

He told her that the next day, he was taking her to get estrogen patches and to start the process of getting her name changed.

 

Switching to the patches was easy and she left with a month’s supply. The name change was a lot more complicated.

They had downloaded the required forms and filled them out the night before. Dean took her to see his lawyer, which was required. The lawyer looked over everything and said that they were all in order. Next they went to the District Court and filed the papers, plus he paid $175.

They were given a court division assignment and a case number. She found out what the notice requirement was. She had to post an ad in the newspaper once a week for the next three weeks, so he took her to the newspaper office and made the arrangements and paid for those too.

Then it was just a matter of waiting. Cassie was emotionally exhausted by the time they were done, so he took her home and put her in bed for a nap, then he went to work.

Cassie laid in the bed, chewing her lip and worrying. She had hidden so well from her family, the ones that she told Dean were dead. What if they saw the ads? What if they were still looking for her? She felt that old familiar knot in her stomach.

She drifted off to sleep.

 


	11. Chapter 11

When she woke up, she realized she’d been sleeping for three hours. Her phone was beeping that she had text messages. They were all from Dean.

**2 PM from Move in with me**

**3PM Move in with me**

**4 PM Dammit woman, move in with me!**

And just then she got another.

**5 PM I’m on my way over. And oh yeah… MOVE IN WITH ME**

Chuckling, she got up and tried to make herself presentable. She ran to the door when he knocked. He came in and swept her up in a passionate kiss.

“Move in with me!”

She laughed. “I’m considering it.”

He grinned. “Well, that’s a slight improvement, I guess.”

 

They made out for a bit, until Dean groaned. “Oh baby, I can’t have you in my arms without wanting to shove my cock up your pretty ass.”

Cassie laughed. “My you _are_ a sweet talker.”

Dean started to move her blouse down but she swatted his hand away. “Oh no, big boy. I’m hungry. I could make us dinner.”

Dean shook his head. “Nope, I’m taking you out. Grab some stuff, you’re spending the night at my place.”

Cassie secretly loved when he got bossy. She jumped up and grabbed a bag. She put in a change of clothes and some essentials. She walked back out to find him on his phone. Hers immediately chimed.

**Move in with me!**

She just laughed and shook her head.

 

In the end, they just decided to call for pizza and have some beer.

Cassie groaned. “I’m going to gain weight if I keep eating like this.”

Dean looked her up and down and said, “You could use some meat on your bones. You’re too thin.”

Cassie just snorted.

 

 

Dean went to the bathroom. Cassie’s phone chimed with another **Move in with me woman!**

Cassie sighed. What a dork.

 

 

It was about six in the morning. Cassie was still sleeping, Dean woke up. He had to piss in the worst way, so he eased out of bed without disturbing her and wandered to the bathroom.

He was just finishing up when he heard a phone ringing in the living room. Still half asleep, he walked to the table by the couch and grabbed the phone without realizing it was Cassie’s.

“Hello?

A man ‘s voice said, “I need to speak to James Milton.”

Dean just said, “Sorry buddy, you got the wrong number.”

The guy made a growling sound and said, “Oh fuck, I guess he’s calling himself Cassie these days. Cassie, uh, Newark? Wait.”

Dean heard the rustling of papers.

The man returned to say, “Novak. Cassie Novak.”

Dean just woke up, “She’s not available. Got a message, buddy?”

The man asked rudely, “Who the fuck am I talking to?’

Dean was getting mad. “My name is Dean Winchester. I’m Cassie’s fiancé.” Not technically true but true enough for this jerk.

The man laughed. “Her fiancé, huh? So she finally caught herself a fag.”

Dean was livid. “Now listen here you bag of dicks…”

The guy cut him off. “Listen. I’m Michael, Jimmy’s brother. Just tell him that our mother died. The funeral is Friday and he knows how to get in touch with me.” He hung up.

Dean had to sit down.

Cassie had told him that all of her family was dead. After talking to this guy, Dean kind of understood why, but he was really hurt that she lied to him. He was confused as to what to do with the information.

Sighing, Dean walked back to the bedroom. He looked at Cassie, sleeping peacefully. She looked so beautiful.

Dean sat on the edge of the bed and said quietly, “Cassie? Baby, wake up.”

Cassie was awake instantly. “What’s wrong? Did something happen?” Her heart was in her throat.

Dean sighed. “Baby, I accidentally answered your phone when I got up to take a piss.”

Cassie’s eyes looked frantic.

“It was… was your brother, Michael.”

Cassie looked terrified. “My bother? He called me?”

It hurt Dean to see the look in her eyes, sort of like a spooked horse.

“Baby, he called to say that your Mother died.”

He figured now was not the time to address her lie.

 

Cassie just sat there for a minute looking completely terrified.

“My brother called me? My mother’s dead?

Dean nodded. “The funeral is Friday if you want to go.”

Cassie started to laugh, but it was more hysteria than amusement.

“Go? Me go there? I’d rather die.”

Dean grabbed her and held her tightly. She was starting to pant.

Dean just ran his hand over her hair and said soothing things to her, trying to calm her. What the hell had those people done to her?

 

She finally calmed. He let go of her and just said quietly, “Baby, what did they do to you?”

Cassie had big tears rolling down her face.

“What didn’t they do is the better question.”

 

 

They sat in the kitchen. Dean had made coffee and Cassie was sipping it. She still had tears in her eyes but was not actively crying.

Sighing, she finally spoke. “I always knew I wasn’t a boy. Always. But my parents were strict, religious. They thought at first they could pray the problem away. When that didn’t work…”

She paused and shuddered.

“They sent me to conversion camps. Three of them over five years. They were… horrible, just unbelievable. When that didn’t work, they told all my brothers that I was sick, evil. They all turned against me. I was banned from going to church because I was deemed an abomination.”

Dean was horrified. He couldn’t think of a thing to say yet that wouldn’t be just a lot of swearing.

“I ran away when I was a senior in high school, and I never looked back. That was the year they tried to have me committed. I’ve been hiding from them ever since. They must have gotten my information from that fucking ad in the newspaper?”

 

 

Dean just went to his knees in front of her. He hugged her tightly and said, “Baby they can never hurt you again. Never. I promise.”

Dean clearly understood now why she had lied about her family.

 


	12. Chapter 12

Cassie said she needed to go home to work. Dean wanted her to stay at his place. He knew she was still frightened and upset, but she wouldn’t hear of it.

“Dean, I have to work. I need to get to my computer.”

Dean told her he’d buy her a laptop.

“You can’t just throw money at all of my problems, Dean. I’ll be fine. I need to go home.”

Reluctantly, he agreed. While she was dressing, he turned the GPS on her phone on. He felt guilty but he just really needed to know that she was safe at home.

 

When Dean left her at home, Cassie got on to her computer and messaged Meg and Balth. She told them that Michael had found her. They were both concerned, but both of them told her she would be safe with Dean.

She told them about how much he wanted her to move in with him. While Meg understood her reluctance, Balth encouraged her to go for it. He told her that she had her own money so if it didn’t work out, she could always find a place and move. She logged off thinking about it.

She worked through the afternoon, and every hour she got a text from Dean asking if she as all right and telling her to move in with him.

 

By the time he got there after work, she had made her decision, but she wanted it to be a surprise. She had fixed dinner for them and he asked about her day. She told him about the blog she was currently working on, and he told her about the latest car they had gotten in to restore.

She casually mentioned that she wanted to come to his office tomorrow and bring him lunch. He said he would love that and they agreed on noon.

 

Later that night as he slept peacefully next to her, she lay awake, both planning how she was going to tell him and being really anxious about her decision.

 

The next morning, he stood at the door, getting ready to do to work. He had her in an embrace, with one hand firmly gripping her ass as he kissed her deeply. When they broke, she reminded him about lunch and he said he was looking forward to it.

 

When she heard the roar of the Impala going down the street, she ran to the computer and messaged Meg. She told her about her plan and Meg was laughing. She told Cassie she really wished there could be pictures.

 

About an hour before time to leave, Cassie started the first part of her plan. She wanted it to have time for her to get used to the feeling, and time to have the desired effect when she got there.

She called a cab to drive her to Dean’s office at eleven forty-five. It let her off in front and she walked boldly in and straight to his office. She told his secretary who she was. The secretary smiled, told her Dean was expecting her and to go on in.

She opened the door and Dean looked up from some paper work and smiled brightly. She turned and locked the door. Dean had a curious look on his face. She went to the one window in the office and pulled the curtains.

Then she stood in the middle of the room with him just looking at her. She had on her old trench coat with the belt tied around her waist. She very slowly untied it.

She let it drop to her shoulders. Dean stood up with his mouth open. She let it drop to the floor, revealing herself in total nudity.

Dean gasped and walked quickly to her. He stopped just short of her and looked her up and down.  He reached and pulled her to him, whispering hot in her ear. “Now _this_ is what I call lunch.”

They kissed passionately. He ran one hand down her spine to her ass. He grabbed a cheek and pulled her even closer. His fingers went to the crack and then he pulled back with his eyes big.

He spun her around and bent her slightly, revealing the plug in her ass. He reached out and touched it, producing a gasp out of her.

“Jesus, baby…” his voice filled with a combination of lust and wonder.

He could hear the smile in her voice as she said, “I knew we only had an hour and I thought this would speed things along.”

He let go of her and walked quickly to his desk. He picked up his phone with one hand, while the other hand was unbuttoning his pants. He pulled the zipper down as he said into the phone, “Hannah, I do not want to be disturbed for the next hour and a half. And I mean, not even if the place is on fire, understood?”

He walked back to her, unbuttoning his shirt. He was naked with her in moments. He pulled her against him and kissed her, exploring her mouth with his tongue and one hand on a breast. The other hand was pressed to the small of her back, holding her against him.

Dean ran his hand over her belly, then he lifted her balls in his hand and ran a finger behind them. Cassie moaned.

He spun her around and bent her over the conference table. He tapped the plug again and listened to her gasp, then he gently pulled it out. There was a lot of lube, making him smile. She really did come prepared.

He put one hand on her hip and the other he used to grasp her shoulder. He pushed the head of his cock past the muscle ring and then all the way into her.

 

Cassie had chosen the plug because it was smaller than Dean’s dick. She needed the burn and the stretch when he entered her. She groaned and pushed back against him, making sure he was as far inside her as possible.

He held there, just feeling how tight she was and how amazing it was to fill her. He honestly felt like he could just stay like this, but he knew she was waiting for him to move. He pulled back very slowly, then thrust back into her again. She pushed back against his thrust and clenched around him.

The sudden tightness made him gasp. He lost it then, and began to ram in and out of her like a man possessed. They were past being quiet and he figured everyone outside his office knew exactly what was happening. He didn’t give a fuck.

Cassie gasped out that she was going to cum, and then she shot string after string of it all over the carpet. The feeling made him cum as well, filling her. He put his head on her back and they both struggled to catch their breath.

As he was pulling out of her, she just said, “The answer is yes.”

He stopped and said, “You mean?”

“Yes, I’ll move in with you.”

 


	13. Chapter 13

He finished pulling out of her, then grabbed her, twirled her around and lifted her off her feet in a huge hug.

“Oh baby, I’m so happy!” He kissed her all over her face with her giggling.

He put her down and went to his private bathroom and brought out a damp cloth to clean them both up. He was grinning like an idiot.

She looked over underneath the conference table. “Uh, we made a mess on your rug.”

He just waved a hand at it and said, “Forget that. How soon can you move?

 

They sat on his couch and discussed logistics. Cassie explained that she’d have to pack up everything she wanted to bring and she would want to put the rest in storage. Secretly she was hedging her bets, thinking that if this didn’t work out she’d still have her furniture.

Dean wanted to hire people to help her. She told him that she wanted to pack her things herself, and then he could get movers to take the rest to storage. He agreed but he was really anxious.

He was thrilled that she said yes, and sort of surprised too. He thought he’d have to pursue it longer.

‘Come on, baby, let’s go to your place and celebrate.” He lifted her from the couch by her hand. She smiled and grabbed her coat from the floor and put it back on. She grabbed the butt plug and shoved it in her pocket, not wanting any employee to find it.

He dressed quickly. He grabbed her by the hand, unlocked his door and walked out. He paused at his secretary’s desk.

“I’m leaving for the day. Make sure janitorial shampoos the rug.” The secretary blushed just a little and said, “Yes Sir.”

 

 

At her house, they actually ate some lunch and discussed what she would take and what she would store. It wasn’t all that much, really, she lived in a small apartment and didn’t have a lot of possessions.

The two most important things to her were her computer and her lap top.

She assured him she would begin packing tomorrow.

He called for pizza for dinner and they sat on the floor in the living room cross legged and ate it and drank beer.

Dean had a bit of a buzz on. He drank more beer than he usually did, sitting and talking with Cassie about moving. He looked at her and felt an ache. He stood up and grabbed her hand, pulling her up from the floor. He scooped her up and carried her to the bedroom.

“I want you now, woman.”

 

She was naked and he only had his boxers on. He was over her, rubbing his hard cock on her belly, loving the feeling of the knit boxers rubbing on him. She moaned and wiggled against him.

“Yeah, baby, you’re a slut for me, aren’t you? Are you my little slut?”

Cassie froze. She began to push against his chest,

“Get off me. Get OFF me… GET OFF!” She pushed against him hard enough to knock him off balance. She struggled from under him, and jumped off the bed.

She began to pant and felt sweaty. All she could hear, echoing in her ear, was, ‘ _slut… slut_ …’

Dean was on the floor next to her. She didn’t even know how she had gotten there. His lips were moving but she couldn’t hear anything he was saying.

_Slut… slut.._

 

Dean was rubbing a circle against the small of her back as she struggled to breathe. She felt like she was drowning. Dean jumped up and came back with a paper bag she held to her mouth.

At last, her breathing steadied. He pulled her into his lap and she rested her head on his chest as she calmed down.

She had tears running down her face.

“Baby, tell me what happened.” He held her gently, not wanting to upset her again in any way.

“It was when you said, ‘slut’. It triggered a bad memory. I’m sorry.”

Dean looked at here. “Why are you sorry? It’s _my_ fault. I’m the one who’s sorry Cas. I… I didn’t know.”

She touched his face. “Of course you didn’t know. It’s just what the guy who... raped me… kept calling me. “

Dean looked completely stricken. “Oh, fuck, baby. I never would have… shit!” He turned away.

She turned his face back to her. “Dean, listen, you aren’t to blame here. You didn’t know, and I understand that. Please don’t beat yourself up over this.”

Dean kissed her. “I will never, ever call you a derogatory name again, I promise.”

Cassie smiled, and grabbed his hand. As she stood up and pulled him up with her, she said, “Now let’s not get hasty. I wouldn’t mind being your little whore…”

She led him back to bed.

 

 

The moving went surprisingly quickly. Cassie was all moved in by the next week. She was especially excited about the kitchen which was all gleaming new, state of the art appliances. She started cooking dinner for them every night.

 

Four days after she moved in, she stood in front of a judge and walked out clutching the court order legally changing her name. She was so excited, and it really made Dean feel wonderful to see her so happy and light-hearted.

He took her to lunch to celebrate. They sat at a booth. She sipped white wine and he pulled on a beer.

“Thank you so much, Dean. This never would have happened without you. It means so much to me… I just can’t believe this is really my name.”

Dean smiled and thought to himself, ‘ _It’s your name until I change it to Cassie Novak Winchester_.’

 

The next few days were busy for Cassie. She notified the blogs she worked for, Social Security, her bank and the DMV of her legal name change. And she chatted with her friends, who were more than thrilled for her. She didn’t tell them about her anxiety attack, because it was over and meaningless to her now.

They settled into an easy routine. She worked on her blogs while he was at work. She cooked for them most nights. He took her out for a date night every weekend.

And the sex was mind blowing.

 


	14. Chapter 14

A month had gone by. Dean just couldn’t wait any longer. He texted Cassie and told her to meet him at the bar where they met, that he’d be there soon.

He walked in and spotted her at the bar immediately. She was sipping a white wine just like she had been the night they met. Grinning, he walked up and took the stool next to her.

“Hi. My name is Dean,”

She turned to him, amusement in her eyes. “Hello. I’m Cassie.”

“Beautiful name. May I buy you another drink?”

She smiled at him with her beautiful eyes shining. “Yes, I think you can.”

After the bartender had given them their drinks, Dean turned to her.

“I love you so much, Cassie. You are the most important thing in my life. I need to have you in my life forever, woman. I want to wake up to you every morning and go to sleep with you in my arms forever. Cassie, will you marry me?”

She had a look of total shock on her face as he slipped off the stool and knelt at her knee. He produced a ring box out of his pocket. He opened it and held it out to her. Inside was a gorgeous diamond engagement ring.

Cassie Just stammered out. “Ye… yes, Dean. I’ll marry you.”

Everyone in the bar began to applaud. They both looked around at all the smiling faces and they both blushed.

Dean stood up and slipped the ring on her finger and pulled her off the stool and into an embrace. He kissed her for a long time.

He whispered in her ear. “Let’s go home and make this official.”

Cassie giggled and they walked to his car hand in hand.

 

But all the way home, Cassie just looked out the window and wondered if this was right. She loved Dean so much, but was he fully prepared to marry a transgendered person? She’d been caught off guard when he asked her and she had been so excited… but maybe she should have thought this through better.

He could never have a child. He risked humiliation if his brother and his friends find out. It will be a matter of public record that he is in what is considered a ‘gay’ marriage.

Cassie chewed her lip and worried.

 

Once they got home. Cassie told Dean she wanted to talk to him. He sat down with a knot forming in his stomach, worried that she’d changed her mind.

“Dean, I wonder if you’ve really thought this through. I mean, marrying me means you’ll never have a child of your own.”

Dean grinned. “I’ve never been sure I wanted kids, Cas. And if we decide we do want them, we can adopt or use a surrogate. Stop worrying,”

Cassie sighed. “And what about your brother? What is he going to think when he finds out?”

Dean just said, “I’m not sure it’s any of Sam’s business, but I’m also confident that he just wants me to be happy. Cas, YOU make me happy.”

“Well, people are bound to find out, it will be listed as a gay marriage.”

Dean just got up, walked to her and hugged her tight. “I said stop worrying. You are the love of my life and the only person, man, woman or trans I want, ever. I’m going to marry you woman, so just get used to it.”

She let him sweep her up in his arms and carry her to the bedroom.

 

Two days later, the local paper did a fluff piece about Dean asking Cassie to marry him in the bar. He got tons of congratulation emails, phone calls and messages. Cassie started to relax,

 

Two days later, vandals trashed Dean’s business. They broke in, scratched up some of the cars, threw paint around and painted terrible things on the walls.

FAG

BUTT FUCKER

TRANNY LOVER

FAGS ARE AN ABOMINATION

It just got worse from there.

Dean walked around with the police and they documented all the damage. He told them he’d call the insurance company in the morning and they assured him they would have a full report ready by noon the next day.

Cassie just stood in the middle of the room with her hand to her mouth. She knew, just _knew_ something like this would happen the second she’d seen that article in the paper. She knew she’d made a huge mistake accepting Dean’s proposal. After all, she knew better than he did just what being with a trans person would lead to.

When Dean was finished, he walked over to Cassie and put his arm around her waist to guide her to the car. She pulled away. He got a very bad feeling but didn’t say anything to her.

 

At home, Cassie just got very quiet. She was so torn. She loved Dean so much and on the one hand, she did feel she deserved happiness. But on the other hand, she was not going to have her happiness at the expense of Dean. She just didn’t know what to do.

At bedtime, she told him she was tired and just turned over. He was shocked. She had never done anything like that before. He realized that the things written on the walls of his business were upsetting to her, so he just let her be.

 

After three days of her saying she was too tired for sex, and being very aloof, Dean was really worried. He didn’t want to confront her yet; he was petrified that she would give him his ring back. He had recently become friends with her best friends Balth and Meg on Facebook, He turned to them for help. He explained what was going on and that he was afraid to ask Cassie about it because she might call off their engagement.

They agreed to chat with her and find out what was going on.

 

 

The next day Dean was dealing with the insurance people at his office. Cassie logged on to her computer and Balth and Meg were waiting for her. They asked what was going on and she told them about her concerns.

Both of them told her that she was overreacting. They assured her that Dean loved her deeply and that he would never regret marrying her. And Meg was adamant about the fact that the vandals messing up his business would just make Dean mad and more determined that they wouldn’t have any effect on his personal life at all.

Cassie had to admit that did sound like Dean. They reminded her how much she loved him and just how much he loved her. They told her how amazing the transformation had been for them to watch, seeing her happy at last.

By the time they logged off, Cassie was ready to talk to Dean about what she had been feeling.

 


	15. Chapter 15

Right before bed, Dean got a test from Meg. He excused himself, pretending it was about work, and read it.

Meg told him that she had been in contact with one of Cassie’s brothers, Gabriel. She said that Gabriel had always felt bad about the way that Cassie was treated by the family, and he really wanted to make it up to her. He was begging Meg to give him Cassie’s address so he could visit.

Dean texted Meg back, asking if she was sure about Gabriel. The last thing Cassie needed right now was being baited by a brother. She was way too fragile since the shop got trashed.

Meg texted back right away. She said that she had been in contact with Gabriel for almost a year and she was sure about him. She said she never would have even brought this up if she hadn’t been convinced of Gabe’s sincerity.

Dean told her he would think about it and let her know soon.

He went to the bedroom, where Cassie was already in bed. She was awake, though, which was an improvement over the past couple of days, where she had pretended to be asleep when he came in although he knew she wasn’t really.

He stripped and got into bed. He was not in the habit of wearing anything to bed. Cassie had on a sheer nightgown that really accentuated her curves and Dean groaned inwardly. But to his surprise, she moved over next to him and put her head on his shoulder. He wrapped an arm around her protectively.

“I think I’m ready to talk this out in the morning, Dean.’

Dean was so relieved. He’s been so worried that she was going to call off the engagement, but this sounded like she was going to explain what was bothering her but still wanted to marry him. Or at least, he hoped so.

He pulled her face up for a kiss. As much as he was aching to make love to her, he didn’t push it.

“I’m so happy to hear that, baby. I just want things to be back to normal around here. I really miss you.”

Cassie sighed. She knew how hard this had been on him and she just wanted to make things better. She wasn’t ready for sex yet, not until after they had talked, but she cuddled up to him and went to sleep in his arms.

 

Cassie woke up early. Dean still had an arm around her. She had one leg thrown over his. She smiled, but she also had to pee so she slowly and carefully moved his arm and her leg. She eased out of the bed and walked quietly to the bathroom. After she peed, she looked at herself in the mirror. She tried to straighten her messy hair but that never worked. Dean swore he loved her hair so she just left it. She made a mental note to change her hormone patch later.

She went back into the bedroom and Dean was awake.

“Gotta piss, I’ll be right back.” He jumped up and Cassie just looked at his erection. His cock was so beautiful, so thick and perfect. It bobbed as he walked and she felt a stirring. She hurriedly pulled on her robe and went to make coffee.

In just a few minutes he was behind her and wrapping his arms around her waist. He had slipped on boxers. He rubbed up against her ass just a little and then accepted the cup of coffee she held out to him.

They sat at the table. Cassie took a sip of coffee.

“Dean, I knew there was going to be trouble the second I read that article about you proposing to me in the bar. I don’t know exactly how it got around that I’m trans but I knew it was going to cause trouble. And when your place got trashed, it felt like it was my fault.”

Dean started to say something but Cassie shushed him. “Let me finish, babe.”

“I know it wasn’t my fault, I mean I know that. But it seems like there is always going to be something that can go wrong. Transgenders aren’t accepted at all. We get beaten and murdered, all the time. I just want to shield you from the ugliness. I love you so much and I hate that you’re going to get hurt by what I am.”

Dean looked angry. “Cas, this is bullshit. I don’t need to be shielded. It’s my job to take care of you, not the other way around. I need you to get this through your head for once and for all. _I don’t care._ I love you more than life, and I am always going to be with you. You can’t get rid of me no matter what you do.”

Dean choked back a sob.

“My business is what I do. You are what I am. You are my heart and soul, Cassie. If there’s trouble, then bring it. As long as I have you, I can face anything.”

 

Cassie was crying too. She got up and embraced Dean, who hugged her to him so tightly she was having trouble breathing. She whispered, “I love you so much. What did I ever do to deserve you?”

Dean kissed her neck. “You are the most beautiful woman in the world, that’s what.”

Dean lifted her up to sit on the counter. He kissed her and as he did, he pulled her robe open and slid it down her arms and off. His hands roamed to her breasts as he probed her mouth with his tongue. It had been a long time for both of them.

They had missed nights, of course, but never more than one. It had been five days since they had sex and they were both so needy at this point.

Dean pulled her nightgown up and pulled her forward. She wrapped her legs around his hips and he lifted her. She pulled the nightgown off and grabbed him around the neck. His strong hands gripped each globe of her ass tightly and pulled them slightly apart.

She felt his hard cock pushing against her belly as he carried her to their bed.

 


	16. Chapter 16

Cassie clung to him. She wanted him so badly. She tried to push herself down on his cock as he carried her.

“No, Cas, don’t. It’ll hurt. Just wait.”

Cas moaned in his ear,” I want it to hurt, Dean, please…”

Dean just said, “No. I won’t hurt you.” He put her on the bed and took off his boxers. He crawled over her, his cock laying heavy on her belly.

He moved down just a bit so that their cocks were rubbing together and Cassie gasped. She clung to him and thrust up to grind harder on him. He groaned…

He wanted her so badly… it had been days. He was so tempted to just thrust into her like she asked him to, but he controlled himself. He really didn’t want to hurt her.

But he fumbled for the lube and dumped way too much into his hand. Dripping lube. He thrust two fingers into her and she arched her back and pushed back against them, telling him silently to give her all of them.

He pushed them in and out and added a third, aching to get his cock in her.

“Please, Dean… please, I’m ready…”

He yanked his fingers out and grabbed his cock. He rubbed the head around her clenching hole and then pushed against it. It resisted at first. Too tight from the days without him. He pushed harder and slipped in.

 

Cassie moaned loudly, pushing against his cock as he was trying to get in her. She thrust back and he was in. She wrapped her legs around him, trying to get him all the way inside her. It hurt a little, burned a lot more, but she loved it, craved it. It had hurt her so much to deny him and herself these past days. But she hadn’t even realized how much she needed this until it was happening.

 

Dean was so desperate; he hadn’t even realized just how much he needed to be in her until now. He knew he was horny but this was like being addicted. He needed her like oxygen. He felt how excruciatingly tight she was around his cock and he groaned with need. He slid all the way into her, pulled her legs up onto his shoulders and bent her in half. He plowed into her harder and faster than he ever had before, just lost in her. He adjusted just a touch and was hitting her prostate with every thrust.

Cassie was already completely gone when Dean started to hit her prostate. She arched her back and let out a long moan that turned into her just saying his name over and over again. Then she could feel it begin. It started as a burn in her groin and spread to her belly. She gasped out. “Dean… Dean I’m gonna cum...”

He felt her shoot cum all over both of them, and she clenched down on his cock so hard he felt like it was in a vise. A hot, slick vise. He thrust in and held, letting his orgasm roll over him and filling her. He just held there for as long as he could, not wanting to pull out. But of course, he softened and slid out. He moved back, unbending her. He sat back on his heels and watched his cum drip out of her. He put fingers to her hole and shoved some back inside her, punching a loud moan out of her. The rest he scooped up on his fingers and put them to her lips. She sucked them with another moan.

 

He laid down and gathered her up in his arms. “I needed that so badly, Cassie. I missed you so fucking much.” Cassie just tucked her head into the space between his neck and his shoulder and snuggled. He laid there, thankful that they were back on track. Then he remembered about her brother coming. He just decided to not say anything. Maybe the guy wouldn’t even show up. But he’d be damned if he was going to say anything to her that might destroy what they just got back.

 

After a bit, Cassie lifted her head and said to him, “I want to taste you. I want you in my mouth.”

She moved down and took his still flaccid dick in her mouth, sucking on the head and causing him to moan. “Just a minute, Cas…”

He grabbed he and flipped her around effortlessly, putting her dick next to his mouth as well. They lay on their sides and took each other into their mouths.

He was already starting to fill, to get hard. He was so thick, if filled her mouth before he was even fully hard. She sucked down as far as she could and back up, licking across his slit to taste his pre cum. He tasted so much like just Dean… she craved him and ran her tongue under the rim of the head and then back down.

She was so smooth and silky in his mouth. He sucked greedily on the head and then just deep-throated her. She bucked into his mouth and he took her in the back of his throat. He held there for a count of ten, until she squirmed and tried to pull back. Then he just went to running his mouth up and down her length.

He put his hand on her ass and pulled her hips even closer. He pulled off her cock and licked over her balls and under them, then back to her cock. She was moaning around his cock in her mouth and it felt delicious. Then she whispered around his dick, “I’m cumming…” She filled his mouth and he swallowed every drop and sucked her thorough her orgasm. When she was done, he just concentrated on her mouth on him.

She lost some of her rhythm when she came, but then she set to work like a madwoman. She swirled her tongue around his shaft and nursed on the head. She used her hand to lift his balls and tug on them, which elicited a groan out of him. Then she slid her hand into his crack and pressed a finger against his anus. He arched his back and came in her mouth. She swallowed it down while she continued to circle his hole with a finger.

 

They just laid there and caught their breath. Then she turned around and lay against him. They fell asleep entwined.

 


	17. Chapter 17

Then next day was Saturday and they cuddled in bed until Dean got hungry so they got up to have breakfast. Dean couldn’t keep his hands off her all the time she was cooking. She ended up swatting him with a spatula.

After breakfast, they cuddled on the couch and watched movies. Things were just getting heated between them when there was a knock on the door. Dean scrambled to put on some pants and let his erection go down while she answered the door.

Dean was in the hall when he heard her say, “Gabriel?”

Dean rushed back, jumping into one pant leg as he ran. He stumbled into the living room and Cassie was still standing at the door. Dean zipped up and went to the door to stand by Cassie.

Gabriel was standing there, looking a little lost. He was short, shorter than Cassie. He had longish brown hair and a beard. His hazel eyes were shining at Cassie.

“I lost track of you after you ran away, Cassie. I’ve been looking for you for years. I can’t believe it’s actually you.”

Cassie had a bewildered look on her face. “You looked for me? Why?”

Gabriel looked guilty. “I always hated the way the family treated you. I just wasn’t brave enough to stand up for you at the time, and for that, I will always be sorry. But after I left home I just wanted to find you and make sure you were alright.”

Dean cleared his throat. He held out his hand. “Hi Gabriel, I’m Dean Winchester. I’m Cassie’s fiancé. Why don’t you come inside and sit down? Let me get you a cup of coffee.” They shook hands.

Cassie smiled and stepped back to let Gabriel in. Dean went to the kitchen to get coffee. Cassie sat on the couch and Gabe sat in a chair opposite her.

“You look beautiful, Cassie.”

Tears began to run down her cheeks. “I never thought I’d ever hear anyone in my family say that, Gabe. Thank you.”

Gabe knelt down on the floor next to her and wiped away her tears. “Don’t cry, Cassie. Please. I’m sorry it took me so long to find you and say those words.”

Dean came back to find them hugging.

 

The afternoon wore away with them talking. It turned out that Gabe had hired a private detective to find Cassie. He had finally tracked her down to the last place she lived before moving to Lawrence. It had also led Gabe to meet Meg. He admitted they had been friends for almost a year. Cassie was amazed that Meg was able to keep that to herself all this time.

It was dinner time and Gabe said he really should go. He hadn’t found a motel yet. Dean convinced him to stay with them.

“You don’t have a lot of time, and you should spend it here with us. We have plenty of room.”

So Gabe agreed. Cassie went to fix dinner and Dean showed Gabe the guest room.

Gabe sat on the bed and asked Dean, “How is she, really? I mean I can see how happy she is with you and I’m really grateful for that. But otherwise, has she been okay?”

Dean sighed. “She had it really hard before she came here. Really hard. But now, I intend to protect her and love her until the day I die. But, she’s still pretty fragile.”

Gabe sighed too. “Yeah, I kind of got that. She always was delicate. She was way too good for our family, that’s for sure. And bless her heart, she was always a girl. You could see it when she was really young. She just got trapped in the wrong body, I guess.”

Then they heard Cassie call them to dinner.

 

Later, Cassie asked about the rest of the family. Gabe told her that Michael was a hot shot lawyer in New York. Raphael was an architect in Chicago. After their mother died, they all lost touch.

And Gabe? He was a television producer on a very popular TV show that filmed in Vancouver.

Cassie smiled so broadly when she heard that. It was one of her favorite shows.

Gabe grinned. “Then, the two of you will just have to come to Vancouver when we’re filming and meet everyone and see what I do for a living.’

Cassie told Dean she really wanted to.

 

Gabe asked if they had set a date yet. Dean said no, there had been a lot going on lately.

Gabe said, “Well, then let me make a suggestion. How about sometime in September? That way, you could honeymoon in Vancouver and see some filming.”

Dean noticed the look on Cassie’s face and said, “I think that’s a great idea, Gabe.”

 

Later, in bed, Dean gathered Cassie up in his arms. “I’m so glad your brother showed up, baby.”

Cassie smiled at his and her eyes sparkled. “Oh so am I. I never thought any of them would ever speak to me again, and now, to have Gabe… it means the world to me.”

Dean hugged her tightly. Then his hand ran down her back to her butt. He squeezed it and then let his fingers travel into the crack. Cassie giggled.

He put her on her back and moved down between her legs. She spread them for him. He pushed her ass up and buried his face in it. He licked across her hole and she gasped. He sat up for a moment and got some lube on his hand. She expected fingers to slide into her, but that was not what happened.

He went back to licking around her anus and then he grabbed her cock with the lubed up hand. He began to jack her off while he teased her hole with his tongue. Cassie moaned and wiggled her hips a little.

Dean pushed his tongue into her and smiled inwardly at her whimper. He continued to play with her cock and tongue in and out of her until she was just wrecked. She managed to gasp out, “I’m… I’m coming…” and filled his hand with her warm silky cum.

He moved up and licked off what spilled on her belly and then moved up further to kiss her. She was a sweaty mess, her hair looked like she had been grabbing it and her eyes were glazed. He was inordinately proud of himself.

He cleaned her up and they slept.

 


	18. Chapter 18

The rest of the weekend with Gabe was enjoyable. He made them laugh with tales of the actors and problems on set. He and Cassie spent time getting to know each other again. It really seemed to be doing Cassie good to have this renewed connection with a member of her family. And anything that made Cassie happy made Dean happy.

 

They had decided on September twentieth for the wedding. Gabe swore he’d be there. They parted with Gabe telling Cassie he was only a phone call away.

 

Cassie was thrilled with making the connection with Gabe. She was also looking forward to giving Meg a really hard time during their next chat.

 

Two days later, Cassie was online with Meg and Balth. Cassie was having a great time pretending she was angry that Meg had befriended Gabe. Meg was trying to defend herself until Cassie let her off the hook.

‘Gabe and I had a wonderful time, Meg. I’m just giving you a hard time for keeping that secret from me for so long.’

Meg answered with a long string of swear words.

Cassie told them that she and Dean had set a date and that they were going to Vancouver for their honeymoon, partially to see the show that Gabe produced. She also told them how important it was to her that they be at her wedding. They promised to try. But Cassie knew both of them had money issues and probably couldn’t afford to come.

 

Later she was telling Dean about the chat, and about how her friends would probably not be able to come for the wedding. Dean put his arm around her and said, “Baby, I want your friends here too. I’ll buy their tickets.”

Cassie was thrilled and showed him just how thrilled she was later in bed.

 

They chose a small non-denominational chapel to get married in. Cassie wanted a fairly traditional wedding. Dean would have been happy to just run to a justice of the peace but he was obviously going to give Cassie whatever she wanted. The wedding would be very small, just close friends, Gabe and Sam.

Cassie was nervous because she hadn’t actually met Sam yet. They had talked on the phone many times and he seemed to like her, but still… she was nervous that when they actually met, things wouldn’t go well.

That was about to be tested. Sam was coming for a weekend to meet her and catch up with Dean.

 

 

Sam was getting off the plane and Cassie and Dean stood watching. Cassie was clutching Dean’s hand so hard her nails dug into his palm.

“Relax, baby, he’s going to love you. You get along great on the phone.”

Cassie just shook her head and didn’t speak.

Finally, Sam was there. He rushed up and grabbed his brother in a huge bear hug and lifted him off his feet. Cassie knew he was tall, but in person he was actually intimidating. Sitting his brother back on his feet, Sam turned to Cassie.

“Hi Cassie. It’s great to finally meet you in person.” He hugged her, but thankfully not as tight as he had hugged Dean.  Then they headed to the car with Sam’s bags. Dean and Sam chatted happily on the way home. Cassie just smiled and listened.

They sat around and Dean and Sam laughed about some stuff from their childhood and talked about stuff they were doing now. Cassie just listened. She got them beer and sat next to Dean on the couch quietly.

Dean was in the bathroom. Sam looked at Cassie and said softly, “You know, I’ve never seen Dean this happy or this relaxed in his life. And it’s all because of you, Cassie. You make my brother very happy.”

Cassie blushed and smiled. “He makes me that happy too, Sam. He’s my world.”

Just then Dean came back in the room and asked if they wanted more beer. But Cassie breathed a sigh of relief. Everything was going to be fine.

 

The weekend went wonderfully. Once she relaxed, she and Sam had a nice time together. When he left, he was all set to be Dean’s best man. Meg was going to stand up with Cassie and Balth was going to be the ring bearer, which they all thought was really funny.

Cassie found the perfect wedding dress in a vintage shop. She carefully hid it from Dean. She also took a trip to a lingerie store to get a surprise for Dean on their wedding night.

The plans were coming along nicely. They had a nice small restaurant reserved for the reception, and a good band to play. There were only going to be twenty people invited to the wedding and the reception so it really was small. But that was just fine with Dean and Cassie.

 

Meg arrived first. Cassie and her squealed and hugged each other tightly. Dean just stood back and laughed at them. Meg was a real beauty, long dark hair and smoldering eyes. She was staying at the house with them. Since there was only one guest room, Balth was getting put up at a hotel. Sam and Gabe were staying at the same one.

 

That night, Meg and Cassie sat up late talking. Meg was telling Cassie just how much she really liked Dean. She was so happy that Cassie had finally found something good, something real. Meg wished she could find the same thing. Cassie just hugged her and told her not to lose hope.

 

The next might was the rehearsal dinner. Meg and Sam were sitting next to one another. Meg kept stealing glances at Sam, and he was doing the same thing when she wasn’t looking. Cassie nudged Dean and pointed at them. Dean grinned really big.

“Hey, Sammy. Cassie and I have something to do later. Could you give Meg a ride back to our place?”

Sam grinned and said, "Sure thing, Dean!”

Dean leaned over and kissed Cassie’s cheek.” Let’s go out for a drink when we leave here, and give them some time alone.”

Right before they went to bed, Sam called Dean on the phone and wanted to know all about Meg. Dean just gave Cassie the thumbs up.

 


	19. Chapter 19

 

 

The morning of the wedding had arrived. Cassie had steadfastly refused to have sex with Dean the night before. She told him they needed a good night’s sleep and anyway, she wanted him really horny for the wedding night. Dean grumbled but went to sleep.

After breakfast, Dean has left to pick up Balth, Gabe and Sam, and go to the chapel to get ready. Meg was helping Cassie get ready. Her dress was beautiful, but what fascinated Meg was what Cassie was wearing underneath. She had black lace panties that she pulled on and tucked her cock up so that just the tip was peeking out over the lace waistband.

Then she had a lacy black garter belt. She pulled on black stockings that had a white bow on the top of the back. She attached them to the garter belt. Meg whistled. When Cassie pulled the dress on there was no hint of any of it.

 

When Dean turned and saw Cassie walking down the aisle, she took his breath away. From her messy hair (He had begged her not to get it done, but just to wear it like it always was) to her amazing dress, she looked perfect. Gabe was walking her to the front, acting as a father to give her away. Meg looked pretty and Sam really made eyes at her.

Following was Balth, carrying a deep purple pillow that held the rings. He had a huge grin on his face.

 

When the vows were over and the minister told Dean he could kiss the bride, he pulled Cassie to him. His hips rubbed up against her crotch and his eyes got big. He kissed her and then whispered in her ear, You’re not tucked?”

Cassie just smiled and slightly shook her head no.

In the car, Dean asked if they really had to go to the reception. He wanted to get her alone and discover what was under her dress. Cassie swatted him arm and assured him they had to go.

Their first dance was to _How Long Will I Love You_ by Ellie Goulding:

 

_How long will I love you?_

_As long as stars are above you_

_And longer, if I can._

_How long will I need you?_

_As long as the seasons need to_

_Follow their plan._

_How long will I be with you?_

_As long as the sea is bound to_

_Wash upon the sand._

_How long will I want you?_

_As long as you want me to_

_And longer by far._

_How long will I hold you?_

_As long as your father told you,_

_As long as you can._

_How long will I give to you?_

_As long as I live through you_

_However long you say._

_How long will I love you?_

_As long as stars are above you_

_And longer, if I may._

_[Spoken:]_

_We're all traveling through time together_

_Every day of our lives._

_All we can do is do our best_

_To relish this remarkable ride._

They did it all, ate, cut the cake and ate a piece, danced. But through it all, Dean was anxious to get her alone. At last, they could leave.

 

They were staying in a hotel that night. Sam and Meg had the house, and their plane didn’t leave until morning. Dean carried her over the threshold and straight to the bed. He sat her on her feet next to it. After kissing her tenderly, he ran his hands over her shoulders and down her arms.

“I love you so much, Cassie Winchester.”

She smiled up at him and said, “Oh, I love you too, husband.” Her heart skipped a beat at the words. _Husband._ She still could hardly believe it.

He pulled her against him and his kiss was more urgent this time. He slipped his tongue into her mouth and played with hers. She wrapped her arms around his back and sighed into the kiss.

He stood back and pulled the dress over her head. She stood still and let him, smiling to think of the reaction she would get when he saw what she had on. And he didn’t disappoint. After the dress was thrown over a chair, he turned back and his mouth fell open.

She stood, with no bra on, and in the lacy black undergarments. His eyes ran over everything and he just moaned. He dropped to his knees and put his mouth on the garter best, and thus the panties underneath. Cassie gasped at his warm, wet mouth on her.

He stood up and scooped her up, depositing her on the bed. He stood up and pulled his clothes off in a hurry, just tossing them aside. When he was naked, Cassie looked at his full cock, dripping pre cum and bobbing up and down as he walked to the bed. He crawled over her, and his cock drug on her belly, leaving a trail of pre cum along her body.

He kissed her deeply and she moaned into his mouth. His hands slid to her breasts, and he cupped them. He kissed down her throat and then to each breast. He took each in his mouth, swirling his tongue around the globe and then nipping and sucking on the nipple. He moved back and forth between them, using his fingers on the one that wasn’t currently in his mouth.

He moved his mouth over her belly, licking and kissing his way down to her garter belt. He lifted his face and smiled at her.

“Can I get these panties off and still keep the garter on?”

Cassie giggled. “I don’t think so.”

He growled, grabbed the lacy panties, pulling at the flimsy material and then just ripped them right off her.

“Dean! What are you do…” She was cut off by his mouth on her cock. “OOOhhhhh…”

He sucked the head of her cock into his mouth. He ran his tongue over the head and shoved the tip into her slit, tasting her pre cum as if it were candy. But then he popped off and sat back on his heels. He lifted one of her legs and ran his hand down the stocking, cupping her calf and running his hand up to the top. He kissed her thigh and then took the other leg and did the same.

Cassie was moaning and reaching out to him. She just needed to touch him, and he moved up so that she could put her palms on his chest. She spread her legs for him, and he looked at her tiny bud of a hole. He reached for the lube.

His own cock was pulsing and throbbing in need. He lubed up his fingers and pushed two into her. She gasped and pushed back on them, fucking herself on them He wiggled them back and forth to open her for his girth.

“Please, Dean, I’m ready…”

 


	20. Chapter 20

Dean couldn’t wait either. He moved up, put her legs over his shoulders and pushed the head of his cock into her. He gasped, never having gotten used to the amazing feeling of just sliding into her. If he was honest, he loved that part the best and sometimes wished he could just pull out and slide back in over and over again. But his need overcame this, and he pushed in all the way.

He moved up, bending her, to get as deep as he possibly could. The feeling of being inside her was mind blowing, mind boggling and not for the first time, he wished this could last forever.

Cassie loved when he first entered her as well. He had such a fat dick and it burned exquisitely. She wanted it to last but it never did, at least not long enough. But then she forgot about the burn because he was pulling back and then he thrust in and it took away all coherent thought.

They moved together like a dance, having fucked a hundred times before but each time was like the first to them. He pulled back and pushed forward in time to her thrusts forward and hold when he pulled back. She dug her fingernails into his back and he groaned at the flash of pain. He bent and kissed her but it was messy and quick.

When at last he could feel himself on the edge, he moved up just a little bit more, hitting her prostate and listening to her moan with every thrust. She gasped out that she was coming and painted them both with spurt after spurt of warm cum.

The feeling of her orgasm, the clench on his cock, drove him over. He thrust in and held, filling her over and over. He put his head on her breasts and panted for air. She held his head in her hands, running her fingers through his hair.

 

When it was done, and they were cleaned up, he held her as if she was precious glass that would break if he moved too quickly. She wrapped herself around him, her leg slung over his and her head on his shoulder. They didn’t speak for a while, just felt the love.

 

 

Their honeymoon was perfect. Vancouver was a beautiful city and they got to meet the actors from their favorite show, even eat dinner with them. They took in the sights but had to go back to the room to make love at least twice a day.

 

They lived pretty much happily ever after. Of course they had their fights, but they always made up before they went to bed, even if it meant staying up half the night. Dean hurt his back and had to give up working on cars, but just had to be satisfied running the business. Cassie’s blogs became the go-to for trans people.

But the love endured, even grew.

And Sam ended up marrying Meg.

 


End file.
